Azo dyes having 2,6-diaminopyridine derivatives as coupling components

ABSTRACT

Azo dyes having 2,6-diaminopyridine derivatives as coupling components which preferably bear cyano or carbamoyl as substituents in the 3-position. The dyes give brilliant yellow to blue colorations, particularly on synthetic polyesters, which are distinguished by outstanding fastness properties.

The invention relates to dyes of the formula (I): ##STR1## in which D isthe radical of a diazo component;

R is unsubstituted or substituted alkyl or unsubstituted or substitutedphenyl;

X is hydrogen, cyano or unsubstituted or substituted carbamoyl;

R¹ is a radical of the formula: C₆ H₅ ; ##STR2## (CH₂)₃ OCH₂ CH₂ OH(CH₂)₃ O(CH₂)₆ OH, ##STR3## (CH₂)₃ OC₂ H₄ OR⁷, (CH₂)₃ (OC₂ H₄)_(q) OR⁸,(CH₂)₃ OR⁹, ##STR4## or the radical containing hydroxyl groups of theformula: ##STR5## R² is hydrogen, R¹ or an unsubstituted or substitutedaliphatic, cycloaliphatic, araliphatic or aryl radical;

R³ is alkyl of one to three carbon atoms or hydroxyalkyl;

R⁴ is hydrogen, alkyl of one to three carbon atoms or hydroxyalkyl;

R⁵ is hydrogen or hydroxy;

R⁶ is hydrogen, alkyl of one to four carbon atoms, methoxy, ethoxy orchloro;

R⁷ is ethyl, propyl, butyl, cyclohexyl, benzyl, phenylethyl ormethylphenyl;

R⁸ is hydrogen, alkyl of one to four carbon atoms, cyclohexyl, phenyl,methylphenyl, benzyl or phenylethyl;

R⁹ is cyclohexyl, phenyl, methylphenyl, benzyl or phenylethyl;

m is 1 or 2;

n is zero, 1 or 2;

q is 2, 3 or 4; and

p is 1, 2, 3 or 4.

The radicals (D) of the diazo components may be derived for example fromamines of the benzene, naphthalene, diphenyl, benzothiazole,benzoisothiazole, thiazole, thiadiazole, thiophene, triazole,benzotriazole, indazole, pyrazole, azobenzene or anthraquinone series.

The following are examples of substituents for the radical (D) of thediazo components: in the benzene series: chloro, bromo, nitro, cyano,trifluoromethyl, methylsulfonyl, ethylsulfonyl, phenylsulfonyl,p-(β-hydroxyethyl)-phenylsulfonyl, carbomethoxy, carboethoxy,carbobutoxy, carbo-β-methoxyethoxy, carbo-β-ethylhexoxy,carbo-β-hydroxyethoxy, carbamoyl, N-substituted carbamoyl,N-disubstituted carbamoyl, N-substituted sulfamoyl, N-disubstitutedsulfamoyl, methyl, ethyl, methoxy and ethoxy;

Examples of N-substituents of carbamoyl or sulfamoyl are methyl, ethyl,propyl, butyl, β-ethylhexyl, cyclohexyl, benzyl, phenylethyl,β-hydroxyethyl, β-hydroxypropyl, β-methoxyethyl, γ-methoxypropyl,γ-ethoxypropyl, pyrrolidide, piperidide and morpholide.

In the azobenzene series; chloro, bromo, nitro, cyano, carbomethoxy,carboethoxy, methyl, ethyl, methoxy, ethoxy, hydroxy, acetylamino,formyl, β-hydroxyethoxy and ethoxycarbonylamino.

In the heterocyclic series; chloro, bromo, nitro, cyano, methyl, ethyl,phenyl, methoxy, ethoxy, methylmercapto, β-carbomethoxyethylmercapto,β-carboethoxyethylmercapto, carbomethoxy, carboethoxy, acetyl,methylsulfonyl and ethylsulfonyl.

The radical D may be derived for example from the following amines:aniline, o-toluidine, m-toluidine, p-toluidine, o-nitroaniline,m-nitroaniline, p-nitroaniline, o-cyanoaniline, m-cyanoaniline,p-cyanoaniline, 2,4-dicyanoaniline, o-chloroaniline, m-chloroaniline,p-chloroaniline, 3,4-dichloroaniline, 2,5-dichloroaniline,2,4,5-trichloroaniline, 2,4,6-trichloroaniline, o-bromoaniline,m-bromoaniline, p-bromoaniline, 2,4,6-tribromoaniline,2-chloro-4-nitroaniline, 2-bromo-4-nitroaniline, 2-cyano-4-nitroaniline,2-methylsulfonyl-4-nitroaniline, 2-methyl-4-nitroaniline,2-methoxy-4-nitroaniline, 4-chloro-2-nitroaniline,4-methyl-2-nitroaniline, 4-methoxy-2-nitroaniline,1-amino-2-trifluoromethyl-4-chlorobenzene, 2-chloro-5-aminobenzonitrile,2-amino-5-chlorobenzonitrile, 1-amino-2-nitrobenzene-4-sulfonic acidn-butylamide, 1-amino-2-nitrobenzene-4-sulfonic acidβ-methoxyethylamide, 2,4-dinitroaniline, 2,4-dinitro-6-chloroaniline,2,4-dinitro-6-bromoaniline, 2,4-dinitro-6-cyanoaniline,1-amino-2,4-dinitrobenzene-6-methylsulfone, 2,6-dichloro-4-nitroaniline,2,6-dibromo-4-nitroaniline, 2-chloro-6-bromo-4-nitroaniline,2,6-dicyano-4-nitroaniline, 2-cyano-4-nitro-6-chloroaniline,2-cyano-4-nitro-6-bromoaniline, 1-aminobenzene-4-methylsulfone,1-amino-2,6-dibromobenzene-4 -methylsulfone,1-amino-2,6-dichlorobenzene-4-methylsulfone,1-amino-2,6-dinitrobenzene-6-carboxylic methyl ester or β-methoxyethylester, propyl 3,5-dichloroanthranilate, β-methoxyethyl3,5-dibromoanthranilate, N-benzoyl-p-phenylenediamine,N-acetyl-p-phenylenediamine, N-phenylsulfonyl-p-phenylenediamine,N-phenylsulfonyl-m-phenylenediamine, 4-aminoacetophenone,4-aminobenzophenone, 2-aminobenzophenone, 2-aminodiphenylsulfone, methyl2-aminobenzoate, methyl 3-aminobenzoate, methyl 4-aminobenzoate and thecorresponding ethyl, propyl, butyl, isobutyl, β-ethylhexyl, cyclohexyl,benzyl, phenyl, β-methoxyethyl, β-ethoxyethyl, β-butoxyethyl, methyldiglycol, ethyl diglycol, methyl triglycol, ethyl triglycol,β-hydroxyethyl, β-acetoxyethyl, β-(β'-hydroxyethoxy)-ethyl,β-hydroxypropyl, γ-hydroxypropyl, ω-hydroxybutyl, ω-hydroxyhexyl esters,methyl 5-nitroanthranilate and the corresponding isobutyl, methyldiglycol, β-methoxyethyl, β-butoxyethyl and β-acetoxyethyl esters of5-nitroanthranilic acid, the dimethyl, diethyl, dipropyl or dibutylester of 3-aminophthalic acid, 4-aminophthalic acid, 5-aminoisophthalicacid or aminoterephthalic acid, the amide, methylamide, propylamide,butylamide, isobutylamide, cyclohexylamide, 62 -ethylhexylamide,γ-methoxypropylamide, α-ethoxypropuylamide or anilide of 3-aminobenzoicacid or 4-aminobenzoic acid, the dimethylamide, diethylamide,pyrrolidide, morpholide or N-methyl-N-β-hydroxyethylamide of2-aminobenzoic acid, 3-aminobenzoic acid or 4-aminobenzoic acid, thediamide or bis-γ-methoxypropylamide of 5-aminoisophthalic acid, thebisdiethylamide of aminoterephthalic acid, the imide,β-hydroxyethylimide, γ-hydroxypropylimide, phenylimide or p-tolylimideof 3-aminophthalic acid or 4-aminophthalic acid, the β-hydroxyethylimideof 3-amino-6-nitrophthalic acid, the dimethylamide, diethylamide,pyrrolidide, morpholide or N-methylanilide of 2-aminobenzenesulfonicacid, 3-aminobenzenesulfonic acid or 4-aminobenzenesulfonic acid,2'-aminophenyl methylsulfonate, 3'-aminophenyl methylsulfonate,4'-aminophenyl methylsulfonate, 2'-aminophenyl ethylsulfonate,3'-aminophenyl ethylsulfonate, 4'-aminophenyl ethylsulfonate,2'-aminophenyl butylsulfonate, 3'-aminophenyl butylsulfonate,4'-aminophenyl butylsulfonate, 2'-aminophenyl benzenesulfonate,3'-aminophenyl benzenesulfonate, 4'-aminophenyl benzenesulfonate, theethylimide, butylimide, β-methoxyethylimide or γ-methoxypropylimide of4-aminonaphthalic acid, 1-aminonaphthalene, 2-aminonaphthalene,1-amino-2-ethoxynaphthalene, 2-aminodiphenyl, 4-aminodiphenyl,1-aminoanthraquinone, 1-amino-4-chloroanthraquinon, 3-aminodiphenyleneoxide, 4-aminodiphenylene oxide, 2-aminobenzothiazole,2-amino-6-methylsulfonylbenzothiazole, 2-amino-6-nitrobenzothiazole,5,6-dichloro-2-aminobenzothiazole, 6,7-dichloro-2-aminobenzothiazole,4-amino-5-bromo-7-nitrol-1,2-benzoisothiazole,3-amino-5-nitro-2,1-benzoisothiazole,3-amino-5-nitro-7-bromo-2,1-benzoisothiazole, 2-aminothiazole,2-amino-5-nitrothiazole, 2-amino-b 4-methylthiazole-5-carboxylic ethylester, 2-amino-4-methyl-5-acetylthiazole,2-amino-3-cyano-4-methylthiophene-5-carboxylic esters,2-phenyl-5-amino-1,3,4-thiadiazole,3-methylmercapto-5-amino-1,2,4-thiadiazole,3-β-carbomethoxyethylmercapto-5-amino-1,2,4-thiadiazole,3-amino-1,2,4-triazole, 4-amino-7-nitrobenzotriazole, 3-aminoindazole,3-amino-5-chloroindazole, 3-amino-5-nitroindazole,1-benzyl-5-aminopyrazole and 1-phenyl-5-aminopyrazole.

Examples of suitable diazo components of the aminoazo series are:2',4-dimethyl-4-aminoazobenzene, 3',2-dimethyl-4-aminoazobenzene,2,5-dimethyl-4-aminoazobenzene, 2-methyl-5-methoxy-4-aminoazobenzene,2-methyl-4',5-dimethoxy-4-aminoazobenzene,4'-chloro-2-methyl-5-methoxy-4-aminoazobenzene,4'-nitro-2-methyl-5-methoxy-4-aminoazobenzene,4'-hydroxy-2-methyl-5-methoxy-4-aminoazobenzene,4'-(β-hydroxyethoxy)-2-methyl-5-methoxy-4-aminoazobenzene,4'-hydroxy-2,2'-dimethyl-5-methoxy-4-aminoazobenzene,4'-hydroxy-4-aminoazobenzene, 4'-hydroxy-2'-methyl-4-aminoazobenzene,4'-hydroxy-3'-methyl-4-aminoazobenzene,2'-hydroxy-5'-methyl-4-aminoazobenzene,4'-hydroxy-2-methoxy-4-aminoazobenzene,4'-hydroxy-2'-chloro-4-aminoazobenzene,4'-hydroxy-2,5-dimethoxy-4-aminoazobenzene,4'-hydroxy-2,6-dichloro-4-aminoazobenzene,4-hydroxy-3-methoxy-4-aminoazobenzene,4'-chloro-2-methyl-4-aminoazobenzene,4'-formyl-2-methyl-4-aminoazobenzene,4'-(ethoxycarbonylamino)-2-methyl-4-aminoazobenzene,2,5-dimethoxy-4-aminoazobenzene, 4'-chloro-2,5-dimethoxy-4-aminoazobenzene,4'-nitro-2,5-dimethoxy-4-aminoazobenzene,4'-(hydroxyethoxy)-2,5-dimethoxy-4-aminoazobenzene,4'-chloro-2,5-dimethyl-4-aminoazobenzene,4'-methoxy-2,5-dimethyl-4-aminoazobenzene, 4'-nitro-4-aminoazobenzene,3,5-dibromo-4-aminoazobenzene, 2,3'-dichloro-4-aminoazobenzene,3-methoxy-4-aminoazobenzene, 1-phenylazo-4-aminonaphthalene and2-phenylazo-3-ethoxy-4-aminonaphthalene.

Examples of radicals R are ethyl, n-propyl, isopropyl, butyl, pentyl,α-ethylpentyl, phenyl, methylphenyl and preferably methyl.

Examples of substituted carbamoyl radicals for X are N-methylcarbamoyl,N-ethylcarbamoyl, N-butylcarbamoyl, N-β-hydroxyethylcarbamoyl,N-γ-methoxypropylacarbamoyl, N,N-dimethylcarbamoyl,N,N-diethylcarbamoyl, N,N-dibutylcarbamoyl orN-methyl-N-β-hydroxyethylcarbamoyl. Unsubstituted carbamoyl is preferredbecause of its easier accessibility.

Examples of individual radicals R¹, in addition to those alreadyspecified, are: (CH₂)₃ OC₂ H₄ OC₂ H₅, (CH₂)₃ OC₂ H₄ --OCH(CH₃)₂, (CH₂)₃OC₂ H₄ OC₄ H₉, (CH₂)₃ OC₂ H₄ OCH₂ C₆ H₅, (CH₂)₃ OC₂ H₄ OC₂ H₄ C₆ H₅,##STR6## (CH₂)₃ (OC₂ H₄)₂ OCH₃, ##STR7## and the corresponding radicalsin which the grouping --OC₂ H₄ --, ##STR8## is present twice, thrice orfour times, and compounds in which C₆ H₅ has been replaced by C₆ H₄ CH₃.

Other examples are: (CH₂)₃ OC₆ H₅, (CH₂)₃ OCH₂ C₆ H₅, (CH₂)₃ OC₂ H₄ C₆H₅, ##STR9## and the radicals having C₆ H₄ CH₃ instead of C₆ H₅.

Radicals R² (in addition to being hydrogen or R¹) may for example bealkyl of one to eight carbon atoms which may be interrupted by oxygenatoms and may bear hydroxy, alkoxy, acyloxy, carboxy, carboxylic ester,cycloalkoxy, aralkoxy or aroxy as substituents, cycloalkyl of five toeight carbon atoms which may bear hydroxy, chloro, hydroxyalkyl,chloroalkyl or alkyl as substituents, aralkyl of seven to fifteen carbonatoms, phenyl which may bear chloro, hydroxy, alkoxy, alkyl,hydroxyalkyl or hydroxyalkoxy as substituents, and also alkenyl,pyrrolidonyalkyl and carboxyalkyl.

Examples of radicals R² are: unsubstituted or substituted alkylradicals: CH₃, C₂ H₅, n- and i-C₃ H₇, n- and i-C₄ H₉, C₆ H₁₃, ##STR10##CH₂ CH=CH₂, CH₂ CH₂ OH, (CH₂)₃ OH, (CH₂)₄ OH, (CH₂)₆ OH, (CH₂)₂ O(CH₂)₂OH, (CH₂)₃ O(CH₂)₄ OH, ##STR11## (CH₂)₃ OC₂ H₄ OCH₃, (CH₂)₃ OC₂ H₄ OC₆H₅, CH₂ CH₂ OCH₃, CH₂ CH₂ OC₂ H₅, CH₂ Ch₂ OC₃ H₇, CH₂ CH₂ OC₄ H₉, (CH₂)₃OCH₃, (CH₂)₃ OC₂ H₅, (CH₂)₃ OC₃ H₇, (CH₂)₃ OC₄ H₉, (CH₂)₃ OC₆ H₁₃,(CH₂)₃ OC₈ H₁₇, ##STR12## carboxyalkyl and carbalkoxyalkyl radicals ofthe formulae: CH₂ --COOE, CH₂ --CH₂ --COOE, (CH₂)₅ --COOE or (CH₂)₂--O--CO--(CH₂)₂ --COOE where E may be for example hydrogen, methyl,ethyl, propyl, benzyl, β-hydroxyethyl, ω-hydroxyhexyl, δ-hydroxybutyl,β-methoxyethyl, γ-methoxypropyl, γ-ethoxypropyl, β-phenoxyethyl orβ-hydroxyethoxyethyl; acyloxyalkyl radicals of the formulae: CH₂ --CH₂--O--acyl, (CH₂)₃ --O--acyl, ##STR13## (CH₂)₆ --O--acyl, (CH₂)₂--O--(CH₂)₂ --O--acyl or (CH₂)₃ --O--(CH₂)₄ --O--acyl in which acyl isfor example CO--H, CO--CH₃, CO--C₂ H₅, ##STR14## CO--CH₂ Cl, CO--CH₂--CO--CH₃, CO--CH=CH₂, ##STR15## CO--CH=CH--COOH, CO--(CH₂)₂ --COOH,CO--(CH₂)₂ --COOC₂ H₅, ##STR16## and the radicals R¹ containing ahydroxyl group may similarly be esterified with acyl.

Acyl radicals also include COOV and CONHB in which B may be for examplealkyl or aryl. Examples are COOCH₃, COOC₂ H₅, COOC₄ H₉, CONCH₃, CONHC₄H₉, CONHC₆ H₅, CONHC₆ H₄ Cl and CONH-C₆ H₃ Cl₂ ; pyrrolidonylalkylradicals of the formulae: ##STR17## cycloalkyl radicals of the formulae:##STR18## aralkyl radicals of the formulae: CH₂ --C₆ H₅, C₂ H₄ --C₆ H₅,##STR19## and with C₆ H₄ --CH₃ instead of C₆ H₅ and the radicals of theformulae:

C₆ h₄ cl, C₆ H₃ Cl₂, C₆ Cl₄ CH₃, C₆ H₃ (CH₃)₂, C₆ H₄ CN, C₆ H₄ OH, C₆ H₄OCH₂ CH₂ OH, C₆ H₄ OCH₃, C₆ H₄ OC₂ H₅ and C₆ H₄ NHCOCH₃.

Dyes of the formula (I) may be produced by reacting a diazo compound ofan amine of the formula (II):

    d--nh.sub.2                                                (ii)

with a coupling component of the formula (III): ##STR20## in which D, R,X, R¹ and R² have the meanings given above.

Diazotization of the amines is carried out conventionally. Coupling isalso carried out conventionally in aqueous medium with or without theaddition of solvents at a weakly to strongly acid pH.

Production of the coupling components of the formula (III) is describedin principle in German Patent Specification No. 2,062,717 and thestatements therein may be applied in the present case.

If the dye of formula (I) of the invention contains an ester group inthe radical R¹ and/or R² the compounds of formula (I) may in principlebe prepared by the said process if the appropriate ester group isalready contained in the coupling component. In some cases however it isconvenient to introduce the acid radical (acyl) into the finished dye offormula (I). The free acids, their anhydrides, chlorides or esters aresuitable for this and conveniently an inert diluent or solvent is addedsuch as monochlorobenzene, dichlorobenzene or trichlorobenzene,tetrahydrofuran, dioxane, dimethylformamide, N-methylpyrrolidone orpyridine.

In esterification with the free acid it may be advantageous to add aninorganic or organic catalyst, for example hydrogen chloride gas orp-toluenesulfonic acid and to allow the water formed to escape byevaporation from the reaction mixture. When an acid anhydride orchloride is used for esterification, the acid itself may in specialcases be used as the solvent. Thus reaction with acetic anhydride may becarried out in glacial acetic acid. When using an acid chloride as theesterifying agent it is advantageous to add an acid-binding agent, forexample sodium carbonate, sodium acetate, magnesium oxide or pyridine tothe reaction mixture. The following are specific examples of esterifyingagents: formic acid, acetic acid, chloroacetic acid and the esters,anhydrides and chlorides of these acids, also chloroformates, diketeneor isocyanates. Conversion of the carboxyl group into the carboxylicester group may similarly be carried out in the finished dye byconventional methods known from the literature.

Particular industrial value attaches to dyes and mixtures of dyes of theformula (Ia): ##STR21## in which Y is nitro, cyano, chloro, bromo,carbomethoxy, carboethoxy, β-methoxycarboethoxy, methylsulfonyl,ethylsulfonyl, methyl, methoxy or phenylazo;

Y¹ is hydrogen, nitro, chloro, bromo, cyano, methyl, methoxy,carbomethoxy, carboethoxy, methylsulfonyl or ethylsulfonyl;

Y² is hydrogen, chloro, bromo, cyano, methyl, methoxy, carbomethoxy orcarboxethoxy;

one A¹ may be a radical of the formula R¹ and the other A¹ may behydrogen or a radical containing a hydroxyl or alkoxy group and thehydroxyl group may be esterified by formyl or acetyl.

Preferred radicals R¹ are for example: C₆ H₅, ##STR22## (CH₂)₃ --OC₂ H₄OH, (CH₂)₃ O(CH₂)₆ OH, ##STR23## (CH₂)₃ OC₂ H₄ OC₆ H₅, ##STR24## (CH₂)₃OC₂ H₄ OCH₂ C₆ H₅, (CH₂)₃ (OC₂ H₄)₂ OR⁸, ##STR25## (CH₂)₃ OC₆ H₅, (CH₂)₃OCH₂ C₆ H₅ and (CH₂)₃ OC₂ H₄ C₆ H₅, R₈ having the meanings given above.

Examples of other preferred radicals A¹ are hydrogen, ω-hydroxybutyl,ω-hydroxyhexyl, β-hydroxyethyl, β-hydroxypropyl and radicals of theformulae:

C₂ h₄ och₃, c₃ h₆ och₃, ch₂ ch₂ ocho, ch₂ ch₂ ch₂ ocho, ch₂ --ch₂--ococh₃, (ch₂)₃ o(ch₂)₄ oh, (ch₂)₂ o(ch₂)₂ oh, ##STR26## (ch₂)₃ or¹⁰,(ch₂)₃ oc₂ h₄ och₃ and (CH₂)₃ OC₂ H₄ OC₆ H₅, R¹⁰ being hydrogen or alkylof one to four carbon atoms. Preferred examples of acyl radicals areCHO, COCH₃ and COC₂ H₅. Moreover the following are preferred: ##STR27##Another group of preferred dyes has the formula: ##STR28## in which D,R¹ and X have the meanings given above.

The radicals R¹ and R² are advantageously chosen so that they contain atleast one hydrogen atom or one or more oxygen atoms and the total numberof carbon atoms is in the range from five to twenty, preferably fromfive to sixteen.

Those dyes are also particularly valuable which contain as dizaocomponents benzothiazole, benzoisothiazole, thiazole, thidadiazole orthiophene which may bear nitro, chloro, bromo, cyano, methyl,methylmercapto, β-carbomethoxyethylmercapto, β-carboethoxyethylmercapto,carbomethoxy, carboethoxy, carboglycol ester or acetyl as substituents.

The following examples are given from among the particularly preferreddiazo components: 4-nitroaniline, 2-chloro-4-nitroaniline,2-bromo-4-nitroaniline, 2-cyano-4-nitronailine,2-methoxy-4-nitroaniline, 2-amino-5-nitrophenylsulfonic aciddimethylamide, 2-amino-5-nitrophenylsulfonic acid butylamide,2-amino-5-nitrophenylsulfonic acid β-methoxyethylamide,2-aminobenzonitrile, 3-chloro-4-aminobenzonitrile,2-chloro-5-aminobenzonitrile, 2-amino-5-chlorobenzonitrile,2,5-dichloro-4-aminobenzonitrile, 1-amino-2,4-dicyanobenzene,1-amino-2,4-dicyano-6-chlorobenzene,2-chloro-4-amino-5-nitrobenzonitrile,2-amino-3-chloro-5-nitrobenzonitrile,1-amino-3-bromo-5-nitrobenzonitrile, 2,6-dicyano-4-nitroaniline,2,5-dichloro-4-nitroaniline, 2,6-dichloro-4-nitroaniline,2,6-dibromo-4-nitroaniline, 2-chloro-6-bromo-4-nitroaniline,2,4-dinitroaniline, 2,4-dinitro-6-chloroaniline,2,4-dinitro-6-bromoaniline, 2-amino-3,5-dinitrobenzonitrile,1-amino-4-nitrobenzene-2-methylsulfone,1-amino-4-nitrobenzene-2-ethylsulfone, 4-methylsulfonylaniline,1-amino-2-chlorobenzene-4-methylsulfone,1-amino-2,6-dibromobenzene-4-methylsulfone,1-amino-2,6-dichlorobenzene-4-methylsulfone, 2-aminobenzoic acid esters,4-aminobenzoic acid esters, 2-amino-5-nitrobenzoic acid esters,2-amino-3-chloro-5-nitrobenzoic acid esters, 2-amino-3,5-dichlorobenzoicacid esters, 2-amino-3,5-dibromobenzoic acid esters, methyl2-amino-3,5-dinitrobenzoate, β-methoxyethyl 2-amino-3,5-dinitrobenzoate,diethyl-2-aminoterephthalate, 4-aminoazobenzene,2,3'-dimethyl-4-aminoazobenzene, 2',3-dimethyl-4-aminoazobenzene,2,5-dimethyl-4-aminoazobenzene and 3,5-dibromo-4-aminoazobenzene.

The following are paricularly valuable heterocyclic diazo components:2-amino-5-nitrothiazole, 2-amino-4-methyl-5-nitrothiazole,2-amino-4-methylthiazole-5-carboxylic acid ethyl ester,2-amino-5-phenyl-1,3,4-thiadiazole, 3-phenyl-5-amino-1,2,4-thiadiazole,3-methylmercapto-5-amino-1,2,4-thiadiazole,3-β-carbomethoxyethylmercapto-5-amino-1,2,4-thiadiazole,3-β-carboethoxyethylamercapto-5-amino-1,2,4-thiadiazole,2-amino-6-cyanobenzothiazole, 2-amino-6-carboxylic methyl esterbenzothiazole, 2-amino-6-nitrobenzothiazole,2-amino-3-cyano-4-methylthiophene-5-carboxylic esters,3-amino-5-nitro-2,1-benzoisothiazole,3-amino-5-nitro-7-chloro-2,1-benzoisothiazole,3-amino-5-nitro-7-bromo-2,1-benzoisothiazole,4-amino-7-nitro-1,2-benzoisothiazole,4-amino-5-bromo-1,2-benzoisothiazole,4-amino-5-bromo-7-nitro-1,2-benzoisothiazole,4-amino-5-cyano-7-nitro-1,2-benzoisothiazole and4-amino-5-chloro-7-nitro-1,2-benzoisothiazole.

The new dyes are yellow to blue and are suitable for coloring textilematerials of acrylonitrile polymers, synthetic polyamides, celluloseesters such as secondary cellulose acetate or cellulose triacetate, andparticularly linear polyesters such as polyethylene glycol terephthalateor polymers having a similar chemical constitution. Deep colorations areobtained which are distinguished by outstanding fastness properties.

The following Examples illustrate the invention. Parts and percentagesare by weight unless otherwise stated.

EXAMPLE 1

A mixture of 187 parts of 2,6-dichloro-3-cyano-4-methylpyridine, 200parts of isopropanol and 300 parts of aniline is stirred for eight hoursat about 90° C to 100° C. The mixture is allowed to cool and pouredwhile stirring into about 1500 parts of water, 200 parts of concentratedhydrochloric acid and 200 parts of ice. Stirring is continued foranother hour and the deposited precipitate which probably has theformula: ##STR29## is suction filtered, washed with water until neutraland dried. About 240 parts of a colorless powder is obtained which meltsat 135° to 140° C.

12.2 parts of this powder is stirred with 40 parts ofγ-hydroxypropylamine for six hours at 245° to 160° C. The mixture isthen allowed to cool and after 100 parts of water has been added it isacidified with hydrochloric acid to a pH of from about 0 to 1. Ifnecessary a little glacial acetic acid or dimethylformamide is added anda solution of the coupling component of the probable formula: ##STR30##is obtained. A solution or suspension of this coupling component iscooled to 0° to 3° C by adding ice and a diazonium salt soultion isadded which is obtained as follows: 6.9 parts of p-nitroaniline hasadded to it about 30 parts of concentrated hydrochloric acid (30%) and80 parts of water, the mixture is cooled to 0° C and 15 parts by volumeof 23% sodium nitrite solution is added in portions. The whole isstirred for another two hours, any excess of nitrous acid present isremoved in the usual way and the product is filtered.

The filtrate is added to the coupling mixture and then such an amount ofsodium acetate or caustic soda solution is added gradually whilestirring until the pH of the coupling mixture is from about 2 to 3.Ice-water may be added to the mixture if it is difficult to stir. Aftercoupling is over the mixture is heated to 70° to 80° C, filtered, washedwith water and dried. About 20 parts of a reddish brown powder isobtained of the probable formula: ##STR31## which dissolves indimethylformamide with a red color and dyes polyethylene terephthalatecloth full, clear yellowish red shades having outstanding fastnessproperties.

The following dyes characterized by the diazo and coupling componentsmay be obtained in an analogous manner.

                                      TABLE 1                                     __________________________________________________________________________    Coupling component:                                                            ##STR32##                                                                    __________________________________________________________________________    Example No.                                                                          Diazo component           R.sup.2        Shade                         __________________________________________________________________________            ##STR33##              CH.sub.2CH.sub.2CH.sub.2OCH.sub.3                                                              reddish yellow                3                              CH.sub.2CH.sub.2OH                                                                             yellow                        4                              CH.sub.2C.sub.2CH.sub.2OH                                                                      reddish yellow                5                                                                                                             ##STR34##       reddish yellow                6                              CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                            reddish yellow                7                              CH.sub.2CH.sub.2OCH.sub.3                                                                      yellow                        __________________________________________________________________________            ##STR35##              H                reddish yellow                9                              CH.sub.2CH.sub.2OH                                                                             reddish yellow                10                             CH.sub.2CH.sub.2CH.sub.2OH                                                                     reddish yellow                11                                                                                                            ##STR36##       reddish yellow                12                             CH.sub.2CH.sub. 2OCH.sub.2CH.sub.2OH                                                           reddish                       __________________________________________________________________________                                                    yellow                        13                                                                                    ##STR37##              H                reddish yellow                14                             CH.sub.2CH.sub.2OH                                                                             yellow                        15                             CH.sub.2CH.sub.2CH.sub.2OH                                                                     yellow                        16                                                                                                            ##STR38##       yellow                        17                             CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                            yellow                        __________________________________________________________________________    18                                                                                    ##STR39##              H                yellow                        19                             CH.sub.2CH.sub.2OH                                                                             yellow                        20                             CH.sub.2CH.sub.2CH.sub.2OH                                                                     yellow                        21                                                                                                            ##STR40##       yellow                        22                             CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                            yellow                        __________________________________________________________________________    23                                                                                    ##STR41##              H                reddish orange                24                             CH.sub.2CH.sub.2OH                                                                             yellowish red                 25                             CH.sub.2CH.sub.2CH.sub.2OH                                                                     yellowish red                 26                                                                                                            ##STR42##       yellowish red                 27                             CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                            yellowish                     __________________________________________________________________________                                                    red                           28                                                                                    ##STR43##              H                reddish orange                29                             CH.sub.2CH.sub.2OH                                                                             yellowish red                 30                             CH.sub.2CH.sub.2CH.sub.2OH                                                                     yellowish red                 31                             CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                            yellowish                     __________________________________________________________________________                                                    red                           32                                                                                    ##STR44##              H                orange                        33                             CH.sub.2CH.sub.2OH                                                                             yellowish red                 34                             CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3                                                            yellowish red                 35                                                                                                            ##STR45##       yellowish red                 36                             CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                            yellowish red                 37                             CH.sub.2CH.sub.2OCH.sub.3                                                                      yellowish red                 38                             CH.sub.2CH.sub.2CH.sub.2OCH.sub.3                                                              yellowish red                 39                             CH.sub.2CH.sub.2OCHO                                                                           reddish orange-                                                               yellowish red                 40                              (CH.sub.2).sub.6OH                                                                            yellowish                     __________________________________________________________________________                                                    red                           41                                                                                    ##STR46##              H                yellowish red                 42                             CH.sub.2CH.sub.2OH                                                                             yellowish red                 43                             CH.sub.2CH.sub.2CH.sub.2OH                                                                     yellowish red                 44                             CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                            red                           45                                                                                                            ##STR47##       red                           46                             CH.sub.2CH.sub.2CH.sub.2OCH.sub.3                                                              red                           47                             CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3                                                            red                           __________________________________________________________________________    48                                                                                    ##STR48##              CH.sub.2CH.sub.2OH                                                                             yellowish red                 49                             CH.sub.2CH.sub.2CH.sub.2OH                                                                     yellowish red                 50                             CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                            yellowish                     __________________________________________________________________________                                                    red                           51                                                                                    ##STR49##              CH.sub.2CH.sub.2OH                                                                             red                           52                             CH.sub.2CH.sub.2CH.sub.2OH                                                                     red                           53                             CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                            red                           __________________________________________________________________________    54                                                                                    ##STR50##              CH.sub.2CH.sub.2OH                                                                             yellowish red                 55                             CH.sub.2CH.sub.2CH.sub.2OH                                                                     yellowish red                 56                                                                                    ##STR51##              CH.sub.2CH.sub.2OH                                                                             reddish yellow                57                             CH.sub.2CH.sub.2CH.sub.2OH                                                                     reddish yellow                58                             CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                            reddish                       __________________________________________________________________________                                                    yellow                        59                                                                                    ##STR52##              CH.sub.2CH.sub.2OH                                                                             reddish orange                60                             CH.sub.2CH.sub.2CH.sub.2OH                                                                     reddish orange                61                             CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                            reddish                       __________________________________________________________________________                                                    orange                        62                                                                                    ##STR53##              CH.sub.2CH.sub.2OH                                                                             orange                        63                             CH.sub.2CH.sub.2CH.sub.2OH                                                                     orange                        64                             CH.sub.2CH.sub. 2OCH.sub.2CH.sub.2OH                                                           orange                        __________________________________________________________________________    65                                                                                    ##STR54##              H                orange                        66                             CH.sub.2CH.sub.2OH                                                                             orange                        67                             CH.sub.2CH.sub.2CH.sub.2OH                                                                     orange                        68                             CH.sub.2CH.sub.2CH.sub.2OCH.sub.3                                                              orange                        __________________________________________________________________________    69                                                                                    ##STR55##              CH.sub.2CH.sub.2OH                                                                             yellow                        70                             CH.sub.2CH.sub.2CH.sub.2OH                                                                     yellow                        71                             CH.sub.2CH.sub.2OCH.sub.2CH.sub.2 OH                                                           yellow                        __________________________________________________________________________    72                                                                                    ##STR56##              H                yellow                        73                             CH.sub.2CH.sub.2OH                                                                             orange                        74                             CH.sub.2CH.sub.2CH.sub.2OH                                                                     orange                        75                             CH.sub.2CH.sub.2OCH.sub.2CH.sub.2 OH                                                           orange                        76                             CH.sub.2CH.sub.2OCH.sub.3                                                                      orange                        __________________________________________________________________________    77                                                                                    ##STR57##              CH.sub.2CH.sub.2CH.sub.2OH                                                                     red                           78                             CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                            red                           __________________________________________________________________________    79                                                                                    ##STR58##              CH.sub.2CH.sub.2CH.sub.2OH                                                                     yellowish red                 80                             CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                            yellowish                     __________________________________________________________________________                                                    red                           81                                                                                    ##STR59##              CH.sub.2CH.sub.2OH                                                                             orange                        82                             CH.sub.2CH.sub.2CH.sub.2OH                                                                     orange                        83                             CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                            orange                        __________________________________________________________________________    84                                                                                    ##STR60##              CH.sub.2CH.sub.2OH                                                                             orange                        85                             CH.sub.2CH.sub.2CH.sub.2OH                                                                     orange                        86                                                                                                            ##STR61##       orange                        87                             CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                            orange                        __________________________________________________________________________    88                                                                                    ##STR62##              CH.sub.2CH.sub.2OH                                                                             yellowish orange              89                             CH.sub.2CH.sub.2CH.sub.2OH                                                                     yellowish                                                                     orange                        90                             CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                            yellowish                                                                     orange                        __________________________________________________________________________    91                                                                                    ##STR63##              CH.sub.2CH.sub.2OH                                                                             orange                        92                             CH.sub.2CH.sub.2CH.sub.2OH                                                                     orange                        __________________________________________________________________________    93                                                                                    ##STR64##              CH.sub.2CH.sub.2OH                                                                             orange                        94                             CH.sub.2CH.sub.2CH.sub.2OH                                                                     orange                        __________________________________________________________________________

                                      TABLE 2                                     __________________________________________________________________________    Coupling component:                                                            ##STR65##                                                                    __________________________________________________________________________    Example No.                                                                          Diazo component                                                                             R.sup.1             Shade                                __________________________________________________________________________    95                                                                                    ##STR66##  CH.sub.2CH.sub.2OH    reddish yellow                       96                 CH.sub.2CH.sub.2CH.sub.2OH                                                                          reddish yellow                       97                 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                 reddish yellow                       __________________________________________________________________________    98                                                                                    ##STR67##  CH.sub.2CH.sub.2OH    yellow                               99                 CH.sub.2CH.sub.2CH.sub.2OH                                                                          yellow                               100                CH.sub.2CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                         yellow                               __________________________________________________________________________    101                                                                                   ##STR68##  CH.sub.2CH.sub.2OH    yellow                               102                CH.sub.2CH.sub.2CH.sub.2OH                                                                          yellow                               103                CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                 yellow                               __________________________________________________________________________    104                                                                                   ##STR69##  CH.sub.2CH.sub.2OH    yellowish red                        105                CH.sub.2CH.sub.2CH.sub.2OH                                                                          yellowish red                        106                CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                 yellowish red                        __________________________________________________________________________    107                                                                                   ##STR70##  CH.sub.2CH.sub.2CH.sub.2OH                                                                          yellowish red                        108                CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                 yellowish red                        __________________________________________________________________________    109                                                                                   ##STR71##  CH.sub.2CH.sub.2CH.sub.2OH                                                                          red                                  110                CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                 red                                  __________________________________________________________________________    111                                                                                   ##STR72##  CH.sub.2CH.sub.2CH.sub.2OH                                                                          yellow                               112                CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                 yellow                               __________________________________________________________________________    113                                                                                   ##STR73##  CH.sub.2CH.sub. 2OH   orange                               114                CH.sub.2CH.sub.2CH.sub.2OH                                                                          orange                               115                CH.sub.2CH.sub.2CH.sub.2OCH.sub.3                                                                   orange                               __________________________________________________________________________

EXAMPLE 116

24.4 parts of the reaction product of aniline with2,6-dichloro-3-cyano-4-methylpyridine (see Example 1) is stirred with 80parts of γ-methoxypropylamine for eight hours under superatmosphericpressure at 140° to 160° C and then allowed to cool. 8 parts of 50%caustic soda solution is added and excess γ-methoxypropylamine and waterare distilled off. The residue is treated with 100 parts of 85% sulfuricacid for five hours at 100° C and allowed to cool. The mixture is pouredinto a mixture of about 500 parts of water, 600 parts of ice and 100parts of 50% caustic soda solution. The mixture, which contains thecoupling component of the probable formula: ##STR74## is cooled to 0° Cand a solution of diazotized 3-amino-5-nitro-2,1-benzothiazole (preparedas follows) is then added in portions; 19.5 parts of3-amino-5-nitro-2,1-benzoisothiazole is added in portions while stirringat 15° to 25° C to about 75 to 85 parts of 96% sulfuric acid and thewhole is cooled to 0° to 4° C. 32.5 parts of 23% nitrosylsulfuric acidis then dripped in at the said temperature. Diazotization is over afterstirring for about four hours at 0° to 5° C. After the diazoniumsolution has been added to the coupling mixture the pH of the mixture israised to about 1.5 to 2.5 by adding an acid-binding agent such assodium acetate (or caustic soda solution). It is convenient to add iceand ice-water to achieve efficient stirring at 0° to 5° C. Aftercoupling is over the mixture is heated to 60° to 80° C and theprecipitated dye is suction filtered, washed with hot water and dried.About 40 parts of a black dye powder of the probable formula: ##STR75##is obtained which dissolves in dimethylformamide with a blue color anddyes polyethylene terephthalate cloth greenish blue shades having verygood fastness properties.

EXAMPLE 117

122 parts of the reaction product of aniline with2,6-dichloro-3-cyano-4-methylpyridine (see Example 1) is treated with150 parts of N-methylpyrrolidone and about 1000 parts of 25% ammonia forfifteen hours at 180° C in an autoclave. After cooling the precipitatedproduct having the probable formula: ##STR76## is filtered, washed withwater and dried. About 108 parts of a colorless product is obtained.

22.4 parts of this product is dissolved in about 100 parts of glacialacetic acid, then cooled to 0° to 2° C with ice and some sulfamic acidis added. A solution of diazotized 2-amino-5-nitrobenzonitrile is addedin portions to this coupling mixture at 0° C. The diazo solution isprepared as follows: 16.3 parts of 2-amino-5-nitrobenzonitrile is addedin portions to a mixture, cooled to 0° C, of about 90 parts of 96%sulfuric acid and 32.5 parts of 23% nitrosylsulfuric acid. Afterstirring for about four to five hours at 0° to 4° C the diazotization isover.

In order to carry out coupling rapidly and completely the couplingmixture (which may be diluted with ice and ice-water) is adjusted at 0°to 5° C to pH about 2.5 by adding sodium acetate solution. Aftercoupling is over the mixture is heated to about 80° C, the precipitateddye of the probable formula: ##STR77## is filtered off, washed with hotwater and dried. About 38 parts of a dark brown powder is obtained whichdissolves in dimethylformamide with a red color and dyes polyethyleneterephthalate cloth full pink to red shades having excellent fastnessproperties.

The dyes characterized in the following Table by the diazo and couplingcomponents may be obtained analogously to the methods described inExample 1, 116 and 117.

                                      TABLE 3                                     __________________________________________________________________________    Coupling component                                                             ##STR78##                                                                    __________________________________________________________________________    Example No.                                                                          Diazo component        R.sup.2          Shade                          __________________________________________________________________________    118                                                                                   ##STR79##           CH.sub.2CH.sub.2OH pink                           119                         CH.sub.2 CH.sub.2CH.sub.2OH                                                                      pink                           120                                                                                                        ##STR80##         pink                           121                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              pink                           122                         CH.sub.2CH.sub.2CH.sub.2OCHO                                                                     pink                           123                         CH.sub.2CH.sub.2OCH.sub.3                                                                        pink                           124                         (CH.sub.2).sub.6OH pink                           125                         CH.sub.2CH.sub. 2OCOCH.sub.3                                                                     pink                           __________________________________________________________________________    126                                                                                   ##STR81##           CH.sub.2CH.sub.2OH red                            127                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       red                            128                                                                                                        ##STR82##         red                            129                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              red                            130                         CH.sub.2CH.sub.2OCH.sub.3                                                                        yellowish                      __________________________________________________________________________                                                   red                            131                                                                                   ##STR83##           H                  red                            132                         CH.sub.2CH.sub.2OH red                            133                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       red                            134                                                                                                        ##STR84##         red                            135                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              red                            136                         CH.sub.2CH.sub.2OCH.sub.3                                                                        red                            137                         CH.sub.2CH.sub.2CH.sub.2OCH.sub.3                                                                red                            138                         CH.sub.2CH.sub.2OCOCH.sub.3                                                                      red                            __________________________________________________________________________    139                                                                                   ##STR85##           H                  red                            140                         CH.sub.2CH.sub.2OH red                            141                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       red                            142                                                                                                        ##STR86##         red                            143                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              red                            144                         CH.sub.2CH.sub.2OCH.sub.3                                                                        red                            145                         C.sub.2 H.sub.5    red                            __________________________________________________________________________    146                                                                                   ##STR87##           CH.sub.2CH.sub.2OH red                            147                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       red                            148                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              red                            __________________________________________________________________________    149                                                                                   ##STR88##           CH.sub.2CH.sub.2OH red                            150                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       red                            151                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              red                            __________________________________________________________________________    152                                                                                   ##STR89##           CH.sub.2CH.sub.2OH red                            153                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       red                            __________________________________________________________________________    154                                                                                   ##STR90##           H                  red                            155                         CH.sub.2CH.sub.2OH red                            156                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       red                            157                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              red                            158                         CH.sub.2CH.sub.2OCH.sub.3                                                                        red                            __________________________________________________________________________    159                                                                                   ##STR91##           CH.sub.2CH.sub.2OH reddish brown                  160                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       reddish brown                  161                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              reddish brown                  162                         CH.sub.2CH.sub.2OCOCH.sub.3                                                                      reddish brown                  __________________________________________________________________________    163                                                                                   ##STR92##           CH.sub.2CH.sub.2OH reddish brown                  164                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       reddish brown                  165                                                                                                        ##STR93##         reddish brown                  166                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              reddish brown                  __________________________________________________________________________    167                                                                                   ##STR94##           CH.sub.2CH.sub.2OH reddish brown                  168                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       reddish brown                  169                         CH.sub.2CH.sub.2CH.sub.2OCH.sub.3                                                                reddish brown                  __________________________________________________________________________    170                                                                                   ##STR95##           CH.sub.2CH.sub.2OH violet                         171                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       violet                         172                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              violet                         173                         CH.sub.2CH.sub.2CH.sub.2OCH.sub.3                                                                violet                         __________________________________________________________________________    174                                                                                   ##STR96##           CH.sub.2CH.sub.2OH bluish red                     175                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       bluish red                     __________________________________________________________________________    176                                                                                   ##STR97##           CH.sub.2CH.sub.2OH bluish red                     177                         CH.sub.2CH.sub.2CHOH                                                                             bluish red                     178                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              bluish red                     __________________________________________________________________________    179                                                                                   ##STR98##           CH.sub.2CH.sub.2OH orange                         180                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       orange                         181                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              orange                         __________________________________________________________________________    182                                                                                   ##STR99##           CH.sub.2CH.sub.2OH orange                         183                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       orange                         184                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              orange                         __________________________________________________________________________    185                                                                                   ##STR100##          H                  bluish red                     186                         CH.sub.2CH.sub.2OH red                            187                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       red                            188                                                                                                        ##STR101##        red                            189                         (CH.sub.2).sub.3O(CH.sub.2).sub.4OH                                                              red                            __________________________________________________________________________    190                                                                                   ##STR102##          CH.sub.2CH.sub.2OH reddish blue                   191                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       navy                           192                                                                                                        ##STR103##        navy                           193                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              navy                           194                         (CH.sub.2).sub.6OH navy                           195                         (CH.sub.2).sub.3O(CH.sub.2).sub.4OH                                                              navy                           196                                                                                                        ##STR104##        reddish blue                   __________________________________________________________________________    197                                                                                   ##STR105##          CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              blue                           __________________________________________________________________________    198                                                                                   ##STR106##          CH.sub.2CH.sub.2CH.sub.2OH                                                                       reddish brown                  199                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              reddish brown                  __________________________________________________________________________    200                                                                                   ##STR107##          CH.sub.2CH.sub.2CH.sub.2OH                                                                       yellow                         201                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              yellow                         __________________________________________________________________________    202                                                                                   ##STR108##          CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              yellow                         203                         (CH.sub.2).sub.3OH yellow                         __________________________________________________________________________    204                                                                                   ##STR109##          CH.sub.2CH.sub.2OH violet                         205                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       violet                         206                                                                                                        ##STR110##        violet                         207                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              violet                         __________________________________________________________________________    208                                                                                   ##STR111##           (CH.sub.2).sub.3OH                                                                              violet                         209                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              violet                         __________________________________________________________________________    210                                                                                   ##STR112##          CH.sub.2CH.sub.2CH.sub.2OH                                                                       yellowish red                  211                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              yellowish                      __________________________________________________________________________                                                   red                            212                                                                                   ##STR113##          CH.sub.2CH.sub.2CH.sub.2OH                                                                       yellowish red                  213                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              yellowish                      __________________________________________________________________________                                                   red                            214                                                                                   ##STR114##          CH.sub.2CH.sub.2CH.sub.2OH                                                                       yellowish red                  215                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              yellowish                      __________________________________________________________________________                                                   red                            216                                                                                   ##STR115##          CH.sub.2CH.sub.2OH red                            217                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       red                            218                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              red                            219                         (CH.sub.2).sub.3O(CH.sub.2).sub.4OH                                                              red                            __________________________________________________________________________    220                                                                                   ##STR116##          CH.sub.2CH.sub.2CH.sub.2OH                                                                       violet                         221                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              violet                         222                         (CH.sub.2).sub.3O(CH.sub.2).sub.4OH                                                              violet                         __________________________________________________________________________    223                                                                                   ##STR117##          CH.sub.2CH.sub.2CH.sub.2OH                                                                       violet                         224                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              violet                         __________________________________________________________________________    225                                                                                   ##STR118##          CH.sub.2CH.sub.2CH.sub.2OH                                                                       violet                         226                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              violet                         __________________________________________________________________________    227                                                                                   ##STR119##          CH.sub.2CH.sub.2CH.sub.2OH                                                                       red                            __________________________________________________________________________    228                                                                                   ##STR120##          H                  reddish orange                 229                         CH.sub.2CH.sub.2OH yellowish red                  230                          CH.sub.2CH.sub.2CH.sub.2OH                                                                      yellowish red                  231                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              yellowish                      __________________________________________________________________________                                                   red                            232                                                                                   ##STR121##          CH.sub.2CH.sub.2OH yellowish red                  233                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       yellowish red                  234                                                                                                        ##STR122##        yellowish red                  235                         CHCHOCHCHOH        yellowish red                  236                         H                  reddish orange                 __________________________________________________________________________    237                                                                                   ##STR123##          CH.sub.2CH.sub.2OH violet                         238                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       violet                         239                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              violet                         __________________________________________________________________________    240                                                                                   ##STR124##          CH.sub.2CH.sub.2OH bluish red                     241                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       reddish violet                 242                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              reddish violet                 243                                                                                                        ##STR125##        reddish violet                 __________________________________________________________________________    244                                                                                   ##STR126##          CH.sub.2CH.sub.2OH reddish violet                 245                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       reddish violet                 246                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              reddish violet                 __________________________________________________________________________    247                                                                                   ##STR127##          CH.sub.2CH.sub.2CH.sub.2OH                                                                       red                            __________________________________________________________________________    248                                                                                   ##STR128##          CH.sub.2CH.sub.2CH.sub.2OH                                                                       violet                         249                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              violet                         __________________________________________________________________________    250                                                                                   ##STR129##          CH.sub.2CH.sub.2OH reddish blue                   251                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       reddish blue                   252                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              reddish blue                   __________________________________________________________________________    253                                                                                   ##STR130##          CH.sub.2CH.sub.2CH.sub.2OH                                                                       blue                           __________________________________________________________________________

                                      TABLE 4                                     __________________________________________________________________________    Coupling component                                                             ##STR131##                                                                   Example No.                                                                          Diazo component   R.sup.1              Shade                           __________________________________________________________________________    254                                                                                   ##STR132##       CH.sub.2CH.sub.2OH   red                             255                      CH.sub.2CH.sub.2CH.sub.2OH                                                                         red                             256                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                red                             __________________________________________________________________________    257                                                                                   ##STR133##       H                    pink                            258                      CH.sub.2CH.sub.2OH   red                             259                      CH.sub.2CH.sub.2OCOCH.sub.3                                                                        pink                            260                      CH.sub.2CH.sub.2CH.sub.2OH                                                                         red                             261                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                pink                            262                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCHO                                                              pink                            263                      (CH.sub.2).sub.6OH   red                             __________________________________________________________________________    264                                                                                   ##STR134##       CH.sub.2CH.sub.2CH.sub.2OH                                                                         red                             265                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                red                             __________________________________________________________________________    266                                                                                   ##STR135##       H                    red                             267                      CH.sub.2CH.sub.2OH   red                             268                      CH.sub.2CH.sub.2CH.sub.2OH                                                                         red                             269                                                                                                     ##STR136##          red                             270                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                red                             __________________________________________________________________________    271                                                                                   ##STR137##       CH.sub.2CH.sub.2OH   red                             272                      CH.sub.2CH.sub.2CH.sub.2OH                                                                         red                             273                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2 OH                                                               red                             274                      (CH.sub.2).sub.3O(CH.sub.2).sub.4OH                                                                red                             __________________________________________________________________________    275                                                                                   ##STR138##       CH.sub.2CH.sub.2CH.sub.2OH                                                                         violet                          __________________________________________________________________________    276                                                                                   ##STR139##       CH.sub.2CH.sub.2CH.sub.2OH                                                                         red                             277                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                red                             __________________________________________________________________________    278                                                                                   ##STR140##       CH.sub.2CH.sub.2CH.sub.2OH                                                                         violet                          279                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                violet                          __________________________________________________________________________    280                                                                                   ##STR141##       CH.sub.2CH.sub.2CH.sub.2OH                                                                         navy                            281                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                navy                            __________________________________________________________________________    282                                                                                   ##STR142##       CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                blue                            283                                                                                   ##STR143##       CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                blue                            __________________________________________________________________________    284                                                                                   ##STR144##       CH.sub.2CH.sub.2OH   red                             285                      CH.sub.2CH.sub.2CH.sub.2OH                                                                         red                             286                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                red                             __________________________________________________________________________    287                                                                                   ##STR145##       CH.sub.2CH.sub.2CH.sub.2OH                                                                         violet                          288                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                violet                          __________________________________________________________________________    289                                                                                   ##STR146##       CH.sub.2CH.sub.2CH.sub.2OH                                                                         violet                          290                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                violet                          __________________________________________________________________________    291                                                                                   ##STR147##       CH.sub.2CH.sub.2OCH.sub.2CH.sub.                                                                   red                             __________________________________________________________________________

                                      TABLE 5                                     __________________________________________________________________________    Coupling component:                                                            ##STR148##                                                                   __________________________________________________________________________    Example No.                                                                         Diazo component    R.sup.2              Shade                           __________________________________________________________________________    293                                                                                  ##STR149##      CH.sub.2CH.sub.2OCOCH.sub.3                                                                          red                             294                    CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3                                                                  red                             295                    CH.sub.2CH.sub.2CH.sub.2OH                                                                           red                             296                    CH.sub.2CH.sub.2OCH.sub.3                                                                            red                             __________________________________________________________________________    297                                                                                  ##STR150##      CH.sub.2CH.sub.2OCOCH.sub.3                                                                          bluish red                      298                    CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3                                                                  bluish red                      299                    CH.sub.2CH.sub.2CH.sub.2OH                                                                           bluish red                      300                    CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCOCH.sub.3                                                         bluish red                      301                    CH.sub.2CH.sub.2OCH.sub.2CH.sub.2 OH                                                                 bluish red                      302                    CH.sub.2CH.sub.2OCH.sub.3                                                                            bluish red                      __________________________________________________________________________    303                                                                                  ##STR151##      CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3                                                                  violet                          304                    CH.sub.2CH.sub.2CH.sub.2OH                                                                           violet                          305                    CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCOCH.sub.3                                                         violet                          306                    CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                  violet                          307                    CH.sub.2CH.sub.3       violet                          308                    CH.sub.2CH.sub.2CH.sub.2OCH.sub.3                                                                    violet                          __________________________________________________________________________    309                                                                                  ##STR152##      CH.sub.2CH.sub.2OCOCH.sub.2COCH.sub.3                                                                greenish blue                   310                    CH.sub.2CH.sub.2OCOCH.sub.3                                                                          greenish blue                   311                    CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3                                                                  greenish blue                   312                    CH.sub.2CH.sub.2CH.sub.2OH                                                                           greenish blue                   313                    CH.sub.2CH.sub.2OCH.sub.3                                                                            greenish blue                   314                    CH.sub.2CH.sub.2CH.sub.2OC.sub.2 H.sub.5                                                             greenish blue                   315   CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCHO                                                          greenish blue                                          316                    CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                  greenish blue                   317                    CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCOCH.sub.3                                                         greenish blue                   __________________________________________________________________________    318                                                                                  ##STR153##      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCOCH.sub.3                                                         greenish blue                   __________________________________________________________________________

                                      TABLE 6                                     __________________________________________________________________________    Coupling compoent:                                                             ##STR154##                                                                   Example No.                                                                          Diazo component     R.sup.1             Shade                          __________________________________________________________________________    319                                                                                             ##STR155##                                                                           CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3                                                                 red                            320                      CH.sub.2CH.sub.2CH.sub.2OH                                                                          red                            __________________________________________________________________________    321                                                                                             ##STR156##                                                                           CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3                                                                 bluish red                     322                      CH.sub.2CH.sub.2CH.sub.2OH                                                                          bluish red                     323                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCOCH.sub.3                                                        bluish red                     324                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCHO                                                               bluish red                     __________________________________________________________________________    325                                                                                             ##STR157##                                                                           CH.sub.2CH.sub.2CH.sub.2O COCH.sub.3                                                                violet                         326                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCHO                                                               violet                         327                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCOCH.sub.3                                                        violet                         __________________________________________________________________________    328                                                                                             ##STR158##                                                                           CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3                                                                 greenish blue                  329                      CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.2COCH.sub.3                                                       greenish blue                  330                      CH.sub.2CH.sub.2CH.sub.2OH                                                                          greenish blue                  331                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                 greenish blue                  332                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCHO                                                               greenish blue                  333                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCOCH.sub.3                                                        greenish                       __________________________________________________________________________                                                   blue                           334                                                                                             ##STR159##                                                                           CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCHO                                                               greenish blue                  335                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.                                                                    greenish blue                  336                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                 greenish blue                  337                      (CH.sub.2).sub.3O(CH.sub.2).sub.4OH                                                                 greenish                       __________________________________________________________________________                                                   blue                           338                                                                                             ##STR160##                                                                           CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCOCH.sub.3                                                        greenish blue                  339                      CH.sub.2CH.sub.2OCH.sub.3                                                                           greenish                       __________________________________________________________________________                                                   blue                       

The following dyes may be prepared analogously:

    __________________________________________________________________________    Example No.                                                                   340                                                                                   ##STR161##                               red                          341                                                                                   ##STR162##                               bluish red                   342                                                                                   ##STR163##                               orange                       343                                                                                   ##STR164##                               yellowish                    __________________________________________________________________________                                                     red                      

EXAMPLE 344

11 parts of the dye of the formula: ##STR165## is heated under refluxwith 100 parts by volume of formic acid for four hours. After coolingabout 100 parts of water is added with stirring and the precipitate ofthe formula: ##STR166## which is thrown down is filtered, washed withwater and dried. About 11 parts of a brown powder is obtained whichdissolves in dimethylformamide with a red color and dyes polyethyleneterephthalate cloth pink to red shades of outstanding fastnessproperties.

EXAMPLE 345

A mixture of 187 parts of 2,6-dichloro-3-cyano-4-methylpyridine, 200parts of isopropanol and 300 parts of 2-phenylpropylamine is stirred foreight hours at about 45° to 55° C. The mixture is then allowed to cooland is poured with stirring into about 1500 parts of water, 200 parts ofconcentrated hydrochloric acid and 200 parts of ice. The whole isstirred for another hour and the deposited precipitate of the probableformula: ##STR167## is suction filtered, washed with water until neutraland dried. About 240 parts of a colorless powder is obtained which meltsat 100° to 105° C.

15 parts of this powder is stirred with 40 parts of β-hydroxyethylaminefor six hours at 145° to 160° C. The mixture is then allowed to cool andis acidified with hydrochloric acid to a pH of from about 0 to 1. Ifnecessary some glacial acetic acid or dimethylformamide is added. Asolution of the coupling component of the probable formula: ##STR168##is obtained.

The solution or suspension of this coupling component is cooled to 0° to3° C by adding ice and a diazonium salt solution is added which has beenobtained as follows:

6.9 parts of p-nitroaniline has about 30 parts of concentratedhydrochloric acid (30%) and 80 parts of water added to it and themixture is then cooled to 0° C and 15 parts by volume of 23% sodiumnitrite solution is added in portions. The whole is stirred for anothertwo hours, any excess of nitrous acid present is removed in the usualway, and the whole is filtered.

The filtrate is added to the coupling mixture and then while stirringsuch an amount of sodium acetate is gradually added that the pH of thecoupling mixture is from about 2 to 3. If the mixture is difficult tostir ice-water may be added. When the coupling is ended the mixture isheated to 70° to 80° C, filtered, washed with water and dried. About 20parts of a brown powder of the probable formula: ##STR169## is obtainedwhich dissolves in dimethylformamide with an orange color and dyespolyethylene terephthalate cloth full, clear orange shades ofoutstanding fastness properties.

The following dyes characterized by the diazo and coupling componentsmay be obtained analogously to the methods described:

                                      TABLE 1                                     __________________________________________________________________________     ##STR170##                                                                   __________________________________________________________________________    Example No.                                                                          Diazo component         R.sup.2            Shade                       __________________________________________________________________________    346                                                                                   ##STR171##             H                  yellow                      347                            CH.sub.2CH.sub.2OH yellow                      348                            CH.sub.2CH.sub.2OH yellow                      349                                                                                                           ##STR172##        yellow                      350                            CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              yellow                      351                            CH.sub.2CH.sub.2OCH.sub.3                                                                        yellow                      __________________________________________________________________________    352                                                                                   ##STR173##             H                  yellow                      353                            CH.sub.2CH.sub.2OH yellow                      354                            CH.sub.2CH.sub.2CH.sub.2OH                                                                       yellow                      355                                                                                                           ##STR174##        yellow                      356                            CH.sub.2CH.sub.2OCH.sub.                                                                         yellowb.2OH                 __________________________________________________________________________    357                                                                                   ##STR175##             H                  yellow                      358                            CH.sub.2CH.sub.2OH yellow                      359                            CH.sub.2CH.sub.2CH.sub.2OH                                                                       yellow                      360                                                                                                           ##STR176##        yellow                      361                            CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              yellow                      __________________________________________________________________________    362                                                                                   ##STR177##             yellow                                         363                            CH.sub.2CH.sub.2OH yellow                      364                            CH.sub.2CH.sub.2CH.sub.2OH                                                                       yellow                      365                                                                                                           ##STR178##        yellow                      366                            CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              yellow                      __________________________________________________________________________    367                                                                                   ##STR179##             H                  orange                      368                            CH.sub.2CH.sub.2OH orange                      369                            CH.sub.2CH.sub.2CH.sub.2OH                                                                       orange                      370                                                                                                           ##STR180##        orange                      371                             CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                             orange                      __________________________________________________________________________    372                                                                                   ##STR181##             H                  orange                      373                            CH.sub.2CH.sub.2OH orange                      374                            CH.sub.2CH.sub.2CH.sub.2OH                                                                       orange                      375                            CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              orange                      __________________________________________________________________________    376                                                                                   ##STR182##             H                  orange                      377                            CH.sub.2CH.sub.2OH orange                      378                            CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3                                                              orange                      379                                                                                                           ##STR183##        orange                      380                            CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              orange                      381                            CH.sub.2CH.sub.2OCH.sub.3                                                                        orange                      382                            CH.sub.2CH.sub.2CH.sub.2OCH.sub.3                                                                orange                      383                            CH.sub.2CH.sub.2OCHO                                                                             orange                      384                            (CH.sub.2).sub.6OH orange                      __________________________________________________________________________    385                                                                                   ##STR184##             H                  yellowish red               386                             CH.sub.2CH.sub.2OH                                                                              yellowish red               387                            CH.sub.2CH.sub.2CH.sub.2OH                                                                       yellowish red               388                            CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              yellowish red               389                                                                                                           ##STR185##        yellowish red               390                            CH.sub.2CH.sub.2CH.sub.2OCH.sub.3                                                                yellowish red               391                            CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3                                                              yellowish                   __________________________________________________________________________                                                      red                         392                                                                                   ##STR186##             CH.sub.2CH.sub.2OH yellowish red               393                            CH.sub.2CH.sub.2CH.sub.2OH                                                                       yellowish red               394                            CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              yellowish                   __________________________________________________________________________                                                      red                         395                                                                                   ##STR187##             CH.sub.2CH.sub.2OH yellowish red               396                            CH.sub.2CH.sub.2OH yellowish red               397                            CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              yellowish                   __________________________________________________________________________                                                      red                         398                                                                                   ##STR188##             CH.sub.2CH.sub.2OH orange                      399                            CH.sub.2CH.sub.2CH.sub.2OH                                                                       orange                      __________________________________________________________________________    400                                                                                   ##STR189##             CH.sub.2CH.sub.2OH yellow                      401                            CH.sub.2CH.sub.2CH.sub.2OH                                                                       yellow                      402                            CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              yellow                      __________________________________________________________________________    403                                                                                   ##STR190##             CH.sub.2CH.sub.2OH orange                      404                            CH.sub.2CH.sub.2CH.sub.2OH                                                                       orange                      405                            CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              orange                      __________________________________________________________________________    406                                                                                   ##STR191##             CH.sub.2CH.sub.2OH yellow                      407                            CH.sub.2CH.sub.2CH.sub.2OH                                                                       yellow                      408                            CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              yellow                      __________________________________________________________________________    409                                                                                   ##STR192##             H                  yellow                      410                            CH.sub.2CH.sub.2 OH                                                                              yellow                      411                            CH.sub.2CH.sub.2OH yellow                      412                            CH.sub.2CH.sub.2CH.sub.2OCH.sub.3                                                                yellow                      __________________________________________________________________________    413                                                                                   ##STR193##             CH.sub.2CH.sub.2OH yellow                      414                            CH.sub.2CH.sub.2CH.sub.2OH                                                                       yellow                      415                            CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              yellow                      __________________________________________________________________________    416                                                                                   ##STR194##             H                  yellow                      417                            CH.sub.2CH.sub.2OH yellow                      418                            CH.sub.2CH.sub.2CH.sub.2OH                                                                       yellow                      419                            CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              yellow                      420                            CH.sub.2CH.sub.2OCH.sub.3                                                                        yellow                      __________________________________________________________________________    421                                                                                   ##STR195##             CH.sub.2CH.sub.2CH.sub.2OH                                                                       yellowish red               422                            CH.sub.2CH.sub.2OH yellowish                   __________________________________________________________________________                                                      red                         423                                                                                   ##STR196##             CH.sub.2CH.sub.2CH.sub.2OH                                                                       orange                      424                            CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              orange                      __________________________________________________________________________    425                                                                                   ##STR197##             CH.sub.2CH.sub.2OH yellow                      426                            CH.sub.2CH.sub.2CH.sub.2OH                                                                       yellow                      427                            CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              yellow                      __________________________________________________________________________    428                                                                                   ##STR198##             CH.sub.2CH.sub.2OH yellow                      429                            CH.sub.2CH.sub.2CH.sub.2OH                                                                       yellow                      430                                                                                                           ##STR199##        yellow                      431                            CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              yellow                      __________________________________________________________________________    432                                                                                   ##STR200##             CH.sub.2CH.sub.2OH yellow                      433                            CH.sub.2CH.sub.2CH.sub.2OH                                                                       yellow                      __________________________________________________________________________    434                                                                           435                                                                                   ##STR201##             CH.sub.2CH.sub.2OH yellow                      436                            CH.sub.2CH.sub.2CH.sub.2OH                                                                       yellow                      __________________________________________________________________________    437                                                                                   ##STR202##             CH.sub.2CH.sub.2OH yellow                      438                            CH.sub.2CH.sub.2CH.sub.2OH                                                                       yellow                      __________________________________________________________________________

                                      TABLE 2                                     __________________________________________________________________________    Coupling component:                                                            ##STR203##                                                                   Example                                                                              Diazo component                                                                           R.sub.1             Shade                                  __________________________________________________________________________    439                                                                                   ##STR204## CH.sub.2CH.sub.2OH  yellow                                 440                CH.sub.2CH.sub.2CH.sub.2OH                                                                        yellow                                 441                H                   yellow                                 __________________________________________________________________________    442                                                                                   ##STR205## CH.sub.2CH.sub.2OH  yellow                                 443                CH.sub.2CH.sub.2CH.sub.2OH                                                                        yellow                                 444                CH.sub.2CH.sub.2CH.sub.2O(CH.sub.2).sub.2 OH                                                      yellow                                 __________________________________________________________________________    445                                                                                   ##STR206## CH.sub.2CH.sub.2OH  yellow                                 446                CH.sub.2CH.sub.2CH.sub.2OH                                                                        yellow                                 447                CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                               yellow                                 __________________________________________________________________________    448                                                                                   ##STR207## CH.sub.2CH.sub.2OH  orange                                 449                CH.sub.2CH.sub.2CH.sub.2OH                                                                        orange                                 450                CH.sub.2CH.sub.2O(CH.sub.2).sub.2OH                                                               orange                                 __________________________________________________________________________    451                                                                                   ##STR208## CH.sub.2CH.sub.2CH.sub.2OH                                                                        orange                                 452                CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                               orange                                 __________________________________________________________________________    453                                                                                   ##STR209## CH.sub.2CH.sub.2OH  yellowish                                                                     red                                    454                CH.sub.2CH.sub.2CH.sub.2OH                                                                        yellowish                                                                     red                                    __________________________________________________________________________    455                                                                                   ##STR210## CH.sub.2CH.sub.2CH.sub.2OH                                                                        yellow                                 456                CH.sub.2CH.sub.2O(CH.sub.2).sub.2 OH                                                              yellow                                 __________________________________________________________________________    457                                                                                   ##STR211## CH.sub.2CH.sub.2OH  yellow                                 458                CH.sub.2CH.sub.2CH.sub.2OH                                                                        yellow                                 459                CH.sub.2CH.sub.2CH.sub.2CH.sub.3                                                                  yellow                                 __________________________________________________________________________

EXAMPLE 460

19.5 parts of 3-amino-5-nitro-2,1-benzoisothiazole is added in portionswhile stirring at 15° to 25° C to about 75 to 85 parts of 96% sulfuricacid and the mixture is cooled to 0° to 4° C. 32.5 parts of 23%nitrosylsulfuric acid is then dripped in at this temperature.Diazotization is over after stirring for about three to four hours at 0°to 5° C. The diazonium salt mixture is then added to a solution orsuspension, cooled to 0° C, of 34 parts of the coupling component of theformula: ##STR212## in 50 parts of 30% hydrochloric acid, 500 parts ofwater and 150 parts of glacial acetic acid. Ice and sodium acetate areadded gradually during the coupling so that the temperature of thecoupling mixture does not exceed 5° C and the pH finally is about 2. Theprecipitated dye of the formula: ##STR213## is filtered off, washed withhot water and dried. About 53 parts of a black powder is obtained whichdissolves in dimethylformamide with a reddish blue color.

EXAMPLE 461

50 parts of the powder obtained in Example 460 is stirred with about 200parts of 85 to 95% sulfuric acid for five hours at from 80° to 100° C.The mixture is then poured onto 1500 parts of ice-water, and theprecipitated dye of the formula: ##STR214## is filtered off, washed withwater and dried. About 40 parts of a dark powder is obtained whichdissolves in dimethylformamide with a blue color and dyes polyethyleneterephthalate cloth blue shades.

Dyes characterized in the following Table by the diazo and couplingcomponents may be obtained by methods analogous to those describedabove:

                                      TABLE 3                                     __________________________________________________________________________    Coupling component:                                                            ##STR215##                                                                   __________________________________________________________________________    Example                                                                              Diazo component        R.sup.2          Shade                          __________________________________________________________________________    462                                                                                   ##STR216##          CH.sub.2CH.sub.2OH yellowish red                  463                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       yellowish                                                                     red                            464                                                                                                        ##STR217##        yellowish red                  465                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              yellowish                                                                     red                            466                         CH.sub.2CH.sub.2CH.sub.2OCHO                                                                     yellowish                                                                     red                            467                         H                  yellowish                                                                     red                            468                         (CH.sub.2).sub.6OH yellowish                                                                     red                            469                         CH.sub.2CH.sub.2OCOCH.sub.3                                                                      yellowish red                                                                 red                            __________________________________________________________________________    470                                                                                   ##STR218##          CH.sub.2CH.sub.2OH yellowish red                  471                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       yellowish                                                                     red                            472                                                                                                        ##STR219##        yellowish red                  473                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              yellowish                                                                     red                            474                         H                  yellowish                                                                     red                            __________________________________________________________________________    475                                                                                   ##STR220##          H                  bluish red                     476                         CH.sub.2CH.sub.2OH bluish                                                                        red                            477                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       bluish                                                                        red                            478                                                                                                        ##STR221##        bluish red                     479                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              bluish                                                                        red                            480                         CH.sub.2CH.sub.2OCH.sub.3                                                                        bluish                                                                        red                            481                         CH.sub.2CH.sub.2CH.sub.2OCH.sub.3                                                                bluish                                                                        red                            482                          CH.sub.2CH.sub.2OCOCH.sub.3                                                                     bluish                                                                        red                            __________________________________________________________________________    483                                                                                   ##STR222##          H                  red                            484                         CH.sub.2CH.sub.2OH red                            485                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       red                            486                                                                                                        ##STR223##        red                            487                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              red                            488                         CH.sub.2CH.sub.2OCH.sub.3                                                                        red                            489                         C.sub.2 H.sub.5    red                            __________________________________________________________________________    490                                                                                   ##STR224##          CH.sub.2CH.sub.2OH red                            491                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       red                            492                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              red                            __________________________________________________________________________    493                                                                                   ##STR225##          CH.sub.2CH.sub.2OH red                            494                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       red                            495                          CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                             red                            __________________________________________________________________________    496                                                                                   ##STR226##          CH.sub.2CH.sub.2OH red                            497                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       red                            __________________________________________________________________________    498                                                                                   ##STR227##          H                  red                            499                         CH.sub.2CH.sub.2OH red                            500                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       red                            501                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              red                            502                         CH.sub.2CH.sub.2OCH.sub.3                                                                        red                            __________________________________________________________________________    503                                                                                   ##STR228##          CH.sub.2CH.sub.2OH yellowish red                  504                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       yellowish                                                                     red                            505                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              yellowish                                                                     red                            506                         CH.sub.2CH.sub.2OCOCH.sub.3                                                                      yellowish                                                                     red                            __________________________________________________________________________    507                                                                                   ##STR229##          CH.sub.2CH.sub.2OH yellowish red                  508                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       yellowish                                                                     red                            509                                                                                                        ##STR230##        yellowish red                  510                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              yellowish                                                                     red                            __________________________________________________________________________    511                                                                                   ##STR231##          CH.sub.2CH.sub.2OH yellowish red                  512                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       yellowish                                                                     red                            513                         CH.sub.2CH.sub.2CH.sub.2OCH.sub.3                                                                yellowish                                                                     red                            __________________________________________________________________________    514                                                                                   ##STR232##          CH.sub.2CH.sub.2OH red                            515                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       bluish                                                                        red                            516                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              bluish                                                                        red                            517                         CH.sub.2CH.sub.2CH.sub.2OCH.sub.2                                                                bluish                                                                        red                            __________________________________________________________________________    518                                                                                   ##STR233##          CH.sub.2CH.sub.2OH red                            519                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       red                            __________________________________________________________________________    520                                                                                   ##STR234##          CH.sub.2CH.sub.2OH red                            521                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       red                            522                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              red                            __________________________________________________________________________    523                                                                                   ##STR235##          CH.sub.2CH.sub.2OH yellow                         524                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       yellow                         525                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              yellow                         __________________________________________________________________________    526                                                                                   ##STR236##          CH.sub.2CH.sub.2OH yellow                         527                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       yellow                         528                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              yellow                         __________________________________________________________________________    529                                                                                   ##STR237##          H                  red                            530                         CH.sub.2CH.sub.2OH red                            531                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       red                            532                                                                                                        ##STR238##        red                            533                         (CH.sub.2).sub.3O(CH.sub.2).sub.4OH                                                              red                            __________________________________________________________________________    534                                                                                   ##STR239##          CH.sub.2CH.sub.2OH reddish blue                   535                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       reddish                                                                       blue                           536                                                                                                        ##STR240##        reddish blue                   537                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              reddish                                                                       blue                           __________________________________________________________________________            ##STR241##          (CH.sub.2).sub.6OH reddish blue                   539                         (CH.sub.2).sub.3O(CH.sub.2).sub.4OH                                                              reddish                                                                       blue                           540                                                                                                        ##STR242##        reddish blue                   __________________________________________________________________________    541                                                                                   ##STR243##          CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              blue                           __________________________________________________________________________    542                                                                                   ##STR244##          CH.sub.2CH.sub.2CH.sub.2OH                                                                       yellowish brown                543                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              yellowish                                                                     brown                          __________________________________________________________________________    544                                                                                   ##STR245##          CH.sub.2CH.sub.2CH.sub.2OH                                                                       yellow                         545                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              yellow                         __________________________________________________________________________    546                                                                                   ##STR246##          CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              yellow                         547                         (CH.sub.2).sub.3OH yellow                         __________________________________________________________________________    548                                                                                   ##STR247##          CH.sub.2CH.sub.2OH bluish red                     549                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       bluish                                                                        red                            550                         H                  bluish                                                                        red                            551                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              bluish                                                                        red                            __________________________________________________________________________    552                                                                                   ##STR248##          (CH.sub.2).sub.3OH bluish red                     553                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              bluish                                                                        red                            554                         H                  bluish                                                                        red                            __________________________________________________________________________    555                                                                                   ##STR249##          CH.sub.2CH.sub.2OH yellowish red                  __________________________________________________________________________    556                                                                                   ##STR250##          CH.sub.2CH.sub.2CH.sub.2OH                                                                       yellowish red                  557                         CH.sub.2CH.sub.2OH yellowish                                                                     red                            __________________________________________________________________________    558                                                                                   ##STR251##          CH.sub.2CH.sub.2OH yellowish red                  __________________________________________________________________________    559                                                                                   ##STR252##          H                  bluish red                     560                         CH.sub.2CH.sub.2OH bluish                                                                        red                            561                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       bluish                                                                        red                            562                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              bluish                                                                        red                            563                         (CH.sub.2).sub.3O(CH.sub.2).sub.4OH                                                              bluish                                                                        red                            __________________________________________________________________________    564                                                                                   ##STR253##          CH.sub.2CH.sub.2CH.sub.2OH                                                                       violet                         565                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              violet                         566                         H                  bluish                                                                        red                            __________________________________________________________________________    567                                                                                   ##STR254##          CH.sub.2CH.sub.2CH.sub.2OH                                                                       violet                         568                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              violet                         __________________________________________________________________________    569                                                                                   ##STR255##          CH.sub.2CH.sub.2CH.sub.2OH                                                                       violet                         570                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              violet                         __________________________________________________________________________    571                                                                                   ##STR256##          CH.sub.2CH.sub.2CH.sub.2OH                                                                       red                            __________________________________________________________________________    572                                                                                   ##STR257##          H                  orange                         573                         CH.sub.2CH.sub.2OH orange                         574                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       orange                         575                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              orange                         __________________________________________________________________________    576                                                                                   ##STR258##          CH.sub.2CH.sub.2OH orange                         577                         CH.sub.2CH.sub.2CH.sub. 2OH                                                                      orange                         578                                                                                                        ##STR259##        orange                         579                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              orange                         580                         H                  orange                         __________________________________________________________________________    581                                                                                   ##STR260##          CH.sub.2CH.sub.2OH violet                         582                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       violet                         583                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              violet                         __________________________________________________________________________    584                                                                                   ##STR261##          CH.sub.2CH.sub.2OH bluish red                     585                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       bluish                                                                        red                            586                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              bluish                                                                        red                            587                                                                                                        ##STR262##        bluish red                     __________________________________________________________________________    588                                                                                   ##STR263##          CH.sub.2CH.sub.2OH bluish red                     589                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       bluish                                                                        red                            590                         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              bluish                                                                        red                            __________________________________________________________________________    591                                                                                   ##STR264##          red                                               __________________________________________________________________________    592                                                                                   ##STR265##          CH.sub.2CH.sub.2OH bluish  red                    593                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       bluish                                                                        red                            594                         H                  bluish                                                                        red                            __________________________________________________________________________    595                                                                                   ##STR266##          CH.sub.2CH.sub.2OH violet                         596                         CH.sub.2CH.sub.2CH.sub.2OH                                                                       violet                         __________________________________________________________________________    597                                                                                   ##STR267##          CH.sub.2CH.sub.2CH.sub.2OH                                                                       reddish blue                   __________________________________________________________________________

                                      TABLE 4                                     __________________________________________________________________________    Coupling component:                                                            ##STR268##                                                                   __________________________________________________________________________    Example                                                                            Diazo component R.sup.1               Shade                              __________________________________________________________________________    598                                                                                 ##STR269##     CH.sub.2CH.sub.2OH    yellowish  red                     599                  CH.sub.2CH.sub.2CH.sub.2OH                                                                          "                                  600                  CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                 "                                  __________________________________________________________________________    601                                                                                 ##STR270##     H                     yellowish red                      602                  CH.sub.2CH.sub.2OH    "                                  603                  CH.sub.2CH.sub.2OCOCH.sub.3                                                                         "                                  604                  CH.sub.2CH.sub.2CH.sub.2OH                                                                          "                                  605                  CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                 "                                  606                  CH.sub.2CH.sub.2OCH.sub.2CH.sub.2 OCHO                                                              "                                  607                  (CH.sub.2).sub.6 OH   "                                  __________________________________________________________________________    608                                                                                 ##STR271##     CH.sub.2CH.sub.2CH.sub.2OH                                                                          red                                609                  CH.sub.2CH.sub.2OH    "                                  __________________________________________________________________________    610                                                                                 ##STR272##     H                     red                                611                  CH.sub.2CH.sub.2OH    "                                  612                  CH.sub.2CH.sub.2CH.sub.2OH                                                                          "                                  613                                                                                                 ##STR273##           "                                  614                  CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                 "                                  __________________________________________________________________________    615                                                                                 ##STR274##     CH.sub.2CH.sub.2OH    red                                616                  CH.sub.2CH.sub.2CH.sub.2OH                                                                          "                                  617                  CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                 "                                  618                  (CH.sub.2).sub.3O(CH.sub.2).sub.4OH                                                                 "                                  __________________________________________________________________________    619                                                                                 ##STR275##     CH.sub.2CH.sub.2CH.sub.2OH                                                                          violet                             __________________________________________________________________________    620                                                                                 ##STR276##     CH.sub.2CH.sub.2CH.sub.2OH                                                                          red                                621                  CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                 "                                  __________________________________________________________________________    622                                                                                 ##STR277##     CH.sub.2CH.sub.2CH.sub.2OH                                                                          violet                             623                  CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                 "                                  __________________________________________________________________________    624                                                                                 ##STR278##     CH.sub.2CH.sub.2CH.sub.2OH                                                                          reddish blue                       625                  CH.sub.2CH.sub.2OCH.sub.2CH.sub.2 OH                                                                "                                  __________________________________________________________________________    626                                                                                 ##STR279##     CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                 blue                               __________________________________________________________________________    627                                                                                 ##STR280##     H                     red                                628                  CH.sub.2CH.sub.2OH    red                                629                  CH.sub.2CH.sub.2CH.sub.2OH                                                                          "                                  630                  CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                 "                                  __________________________________________________________________________    631                                                                                 ##STR281##     CH.sub.2CH.sub.2CH.sub.2OH                                                                          bluish red                         632                  CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                 "                                  __________________________________________________________________________    633                                                                                 ##STR282##     CH.sub.2CH.sub.2CH.sub.2OH                                                                          bluish  red                        634                  CH.sub.2 CH.sub.2O(CH.sub.2).sub.2 OH                                                               "                                  __________________________________________________________________________    635                                                                                 ##STR283##     CH.sub.2CH.sub.2CH.sub.2OH                                                                          red                                636                  CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                 "                                  __________________________________________________________________________

                                      table 5                                     __________________________________________________________________________    coupling component                                                             ##STR284##                                                                   __________________________________________________________________________    Example                                                                            Diazo component   R.sup.2                Shade                           __________________________________________________________________________    637                                                                                 ##STR285##       CH.sub.2CH.sub.2OCOCH.sub.3                                                                          red                             638                    CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3                                                                  "                               639                    CH.sub.2CH.sub.2CH.sub.2OH                                                                           "                               640  CH.sub.2CH.sub.2OCH.sub.3                                                                       "                                                      __________________________________________________________________________    641                                                                                 ##STR286##       CH.sub.2CH.sub.2OCOCH.sub.3                                                                          bluish red                      642                    CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3                                                                  "                               643                    CH.sub.2CH.sub.2CH.sub.2OH                                                                           "                               644                    CH.sub.2CH.sub.2OCH.sub.2CH.sub.2 OCOCH.sub.3                                                        "                               645                    CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                  "                               646                    CH.sub.2CH.sub.2OCH.sub.3                                                                            "                               __________________________________________________________________________    647                                                                                 ##STR287##       CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3                                                                  red violet                      648                    CH.sub.2CH.sub.2CH.sub.2OH                                                                           "                               649                    CH.sub.2CH.sub. 2OCH.sub.2CH.sub.2OCOCH.sub.3                                                        "                               650                    CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                  "                               651                    CH.sub.2CH.sub.3       "                               652                    CH.sub.2CH.sub.2CH.sub.2OCH.sub.3                                                                    "                               __________________________________________________________________________    653                                                                                 ##STR288##       CH.sub.2CH.sub.2 OCOCH.sub.2COCH.sub.3                                                               blue                            654                    CH.sub.2CH.sub.2OCOCH.sub.3                            655                    CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3                                                                  "                               656                    CH.sub.2CH.sub.2CH.sub.2OH                                                                           "                               657                    CH.sub.2CH.sub.2OCH.sub.3                                                                            "                               658                    CH.sub.2CH.sub.2CH.sub.2OC.sub.2 H.sub.5                                                             "                               659                    CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCHO                                                                "                               660                    CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                  "                               661                    CH.sub.2CH.sub.OCH.sub.2CH.sub.2OCOCH.sub.3                                                          "                               __________________________________________________________________________    662                                                                                 ##STR289##       CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCOCH.sub.3                                                         greenish blue                   __________________________________________________________________________

                                      TABLE 6                                     __________________________________________________________________________    Coupling component:                                                            ##STR290##                                                                   __________________________________________________________________________    Example                                                                             Diazo component                                                                            R.sup.2             Shade                                  __________________________________________________________________________    663                                                                                  ##STR291##  H                   yellowish red                          664                CH.sub.2CH.sub.2OH  red                                    665                CH.sub.2CH.sub.2CH.sub.2OH                                                                        red                                    666                                                                                               ##STR292##         yellowish red                          667                CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                               yellowish red                          __________________________________________________________________________    668                                                                                  ##STR293##  H                   yellowish red                          669                CH.sub.2CH.sub.2OH  yellowish red                          670                CH.sub. 2CH.sub.2CH.sub.2OH                                                                       yellowish red                          671                CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                               yellowish red                          __________________________________________________________________________    672                                                                                  ##STR294##  H                   orange                                 673                CH.sub.2CH.sub.2OH  orange                                 674                CH.sub.2CH.sub.2CH.sub.2OH                                                                        orange                                 675                CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                               orange                                 __________________________________________________________________________    676                                                                                  ##STR295##  H                   bluish red                             677                CH.sub.2CH.sub.2OH  red                                    678                CH.sub.2CH.sub.2CH.sub.2OH                                                                        red                                    __________________________________________________________________________    679                                                                                  ##STR296##  H                   red                                    680                CH.sub.2CH.sub.2OH  red                                    681                CH.sub.2CH.sub.2CH.sub.2OH                                                                        red                                    __________________________________________________________________________    682                                                                                  ##STR297##  H                   yellow                                 683                CH.sub.2CH.sub.2OH  yellow                                 __________________________________________________________________________

The further diazo components of Examples 345 to 662 give with thecoupling components of the formula above Table 6 on page 46 dyes whichhave only negligible differences from the corresponding dyes with the2-phenylpropylamine radical.

EXAMPLE 684

A mixture of 187 parts of 2,6-dichloro-3-cyano-4-methylpyridine, 150parts of triethylamine, 200 parts of isopropanol and 160 parts of2-amino-6-methylheptanol-(6) is stirred for eight hours at about 55° to80° C. The mixture is then allowed to cool and is poured with stirringinto about 1500 parts of water, 200 parts of concentrated hydrochloricacid and 200 parts of ice. The whole is further stirred for anotherhour, the oil of the probable formula: ##STR298## which separates isdecanted and washed with water. The oil contains a minor amount of2-chloro-3-cyano-4-methyl-6-aminoheptanolpyridine isomer.

15 parts of the oil is stirred with 40 parts of β-hydroxy-ethylamine for6 hours at 145°-160° C, allowed to cool, mixed with 100 parts of waterand acidified with hydrochloric acid to a pH of about 0 to 1. After anynecessary addition of some glacial acetic acid or dimethylformamide, asolution of the coupling component of the probable formula: ##STR299##is obtained which contains a minor amount of the 2,6-dialkylaminoisomer.

The solution of this coupling is cooled to 0 to 3° C by adding ice and adiazonium salt solution is added which has been obtained as follows: 6.9parts of p-nitroaniline has added to it about 30 parts of concentratedhydrochloric acid (30%) and 80 parts of water, then the mixture iscooled to 0° C and 15 parts by volume of 23% sodium nitrate solution isadded in portions. Stirring is continued for another two hours, anyexcess of nitrous acid present is removed as usual and filtrationcarried out.

The filtrate is added to the coupling mixture; then such an amount ofsodium acetate or caustic soda solution is gradually added whilestirring that the pH of the coupling mixture is from about 2 to 3. Ifthe mixture is difficult to stir, ice-water may be added. When couplingis over the mixture is heated to 70° to 80° C, filtered, and the residuewashed with water and dried. About 20 parts of a brown powder isobtained which probably has the formula: ##STR300## (the dye contains aminor proportion of the 2,6-dialkylaminopyridine isomer). It dissolvesin dimethylformamide with an orange color and dyes polyethyleneterephthalate cloth full, clear orange shades having outstandingfastness properties.

The following dyes characterized by the diazo and coupling componentsare obtained analogously to the methods described.

                                      TABLE 1                                     __________________________________________________________________________    Coupling component:                                                            ##STR301##                                                                   Example                                                                            Dizo component            R.sup.2       Shade                            __________________________________________________________________________    685                                                                                 ##STR302##             H               yellow                           686                          CH.sub.2CH.sub.2OH                                                                            yellow                           687                          CH.sub.2CH.sub.2CH.sub.2OH                                                                    yellow                           688                                                                                                         ##STR303##     yellow                           __________________________________________________________________________    689                                                                                 ##STR304##             H               yellow                           690                          CH.sub.2CH.sub.2 OH                                                                           yellow                           691  CH.sub.2CH.sub.2CH.sub.2OH                                                                            yellow                                           692                                                                                                         ##STR305##     yellow                           693                                                                                                         ##STR306##     yellow                           __________________________________________________________________________    694                                                                                 ##STR307##             H               yellow                           695                          CH.sub.2CH.sub.2OH                                                                            yellow                           696                          CH.sub.2CH.sub.2CH.sub.2OH                                                                    yellow                           697                                                                                                         ##STR308##     yellow                           698                                                                                                         ##STR309##                                      699                                                                                 ##STR310##             H               yellow                           700                          CH.sub.2CH.sub.2OH                                                                            yellow                           701                          CH.sub.2CH.sub.2CH.sub.2OH                                                                    yellow                           702                                                                                                         ##STR311##     yellow                           703                                                                                                         ##STR312##     yellow                           __________________________________________________________________________    704                                                                                 ##STR313##             H               orange                           705                          CH.sub.2CH.sub.2OH                                                                            orange                           706                          CH.sub.2CH.sub.2OH                                                                            orange                           707                                                                                                         ##STR314##     orange                           __________________________________________________________________________    708                                                                                 ##STR315##             H               oange                            709                          CH.sub.2CHOH    oragne                           710                          CH.sub.2CH.sub.2OH                                                                            orange                           __________________________________________________________________________    711                                                                                 ##STR316##             H               orange                           712                                                                                                         ##STR317##     orange                           713                          CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3                                                           orange                           714                                                                                                         ##STR318##     orange                           715                          (CH.sub.2).sub.5 COOCH.sub.3                                                                  orange                           716                          CH.sub.2CH.sub.2OCH.sub.3                                                                     orange                           717                          CH.sub.2CH.sub.2CH.sub.2OCH.sub.3                                                             orange                           718                          CH.sub.2CH.sub.2 OCHO                                                                         orange                           719                          (CH.sub.2).sub.6OH                                                                            orange                           __________________________________________________________________________    720                                                                                 ##STR319##             H               yellowish red                    721                          CH.sub.2CH.sub.2OH                                                                            yellowish                                                                     red                              722                          CH.sub.2CH.sub.2CH.sub.2OH                                                                    yellowish                                                                     red                              723                                                                                                         ##STR320##     yellowishred                     724                          CH.sub.2CH.sub.2CH.sub.2OCH.sub.3                                                             yellowish                                                                     red                              __________________________________________________________________________    725                                                                                 ##STR321##             CH.sub.2CH.sub.2OH                                                                            yellowish red                    726                          CH.sub.2CH.sub.2CH.sub.2OH                                                                    yellowish                                                                     red                              __________________________________________________________________________    727                                                                                 ##STR322##             CH.sub.2CH.sub.2OH                                                                            yellowish red                    728                          CH.sub.2CH.sub.2CH.sub.2OH                                                                    yellowish                                                                     red                              __________________________________________________________________________    729                                                                                 ##STR323##             CH.sub.2CH.sub.2OH                                                                            orange                           730                          CH.sub.2CH.sub.2CH.sub.2OH                                                                    orange                           __________________________________________________________________________    731                                                                                 ##STR324##             CH.sub.2CH.sub.2OH                                                                            yellow                           732                          CH.sub.2CH.sub.2CH.sub.2OH                                                                    yellow                           __________________________________________________________________________    733                                                                                 ##STR325##             CH.sub.2CH.sub.2OH                                                                            orange                           734                          CH.sub.2CH.sub.2CH.sub.2OH                                                                    orange                           __________________________________________________________________________    735                                                                                 ##STR326##             CH.sub.2CH.sub.2OH                                                                            yellow                           736                          CH.sub.2CH.sub.2CH.sub.2OH                                                                    yellow                           __________________________________________________________________________    737                                                                                 ##STR327##             H               yellow                           738                          CH.sub.2CH.sub.2OH                                                                            yellow                           739                          CH.sub.2CH.sub.2CH.sub.2OH                                                                    yellow                           __________________________________________________________________________    740                          CH.sub.2CH.sub.2CH.sub.2OCH.sub.3                741                                                                                 ##STR328##             CH.sub.2CHk.sub.2OH                                                                           yellow                           742                          CH.sub.2CH.sub.2CH.sub.2OH                                                                    yellow                           __________________________________________________________________________    743                                                                                 ##STR329##             H               yellow                           744                          CH.sub.2CH.sub.2OH                                                                            yellow                           745                          CH.sub.2CH.sub.2 OH                                                                           yellow                           746                          (CH.sub.2).sub.5 COCH                                                                         yellow                                                                        (polyamide)                      747                          CH.sub.2CH.sub.2OCH.sub.3                                                                     yellow                           __________________________________________________________________________    748                                                                                 ##STR330##             CH.sub.2CH.sub.2CH.sub.2OH                                                                    yellowish red                    749                          CH.sub.2CH.sub.2OH                                                                            yellowish                                                                     red                              __________________________________________________________________________    750                                                                                 ##STR331##             CH.sub.2CH.sub.2CH.sub.2OH                                                                    orange                           __________________________________________________________________________    751                                                                                 ##STR332##                                                              752                          CH.sub.2CH.sub.2CH.sub.2OH                                                                    yellow                           __________________________________________________________________________    753                                                                                 ##STR333##             CH.sub.2CH.sub.2OH                                                                            yellow                           754                          CH.sub.2CH.sub.2CH.sub.2 OH                                                                   yellow                           755                                                                                                         ##STR334##     yellow                           __________________________________________________________________________    756                                                                                 ##STR335##             CH.sub.2CH.sub.2OH                                                                            yellow                           757                                                                                 ##STR336##             CH.sub.2CH.sub.2OH                                                                            yellow                           758                          CH.sub.2CH.sub.2CH.sub.2OH                                                                    yellow                                                        (CH.sub.2).sub.5 COOH                                                                         yellow                                                                        (polyamide)                      __________________________________________________________________________    759                                                                                 ##STR337##             CH.sub.2CH.sub.2OH                                                                            yellow                           760                          CH.sub.2CH.sub.2CH.sub.2OH                                                                    yellow                           __________________________________________________________________________    761                                                                                 ##STR338##             CH.sub.2CH.sub.2OH                                                                            yellow                           762                          CH.sub.2CH.sub.2CH.sub.2OH                                                                    yellow                           __________________________________________________________________________

                                      TABLE 2                                     __________________________________________________________________________    Coupling component:                                                            ##STR339##                                                                   __________________________________________________________________________    Example                                                                            Diazo component                                                                              R.sup.1        Shade                                      __________________________________________________________________________    763                                                                                 ##STR340##    CH.sub.2CH.sub.2OH                                                                           yellow                                     764                 CH.sub.2CH.sub.2CH.sub.2OH                                                                   yellow                                     __________________________________________________________________________    765                                                                                 ##STR341##    H              yellow                                     766                 CH.sub.2CH.sub.2OH                                                                           yellow                                     767                 CH.sub.2CH.sub.2CH.sub.2OH                                                                   yellow                                     __________________________________________________________________________    768                                                                                 ##STR342##    CH.sub.2CH.sub.2OH                                                                           yellow                                     __________________________________________________________________________    769                                                                                 ##STR343##    CH.sub.2CH.sub.2OH                                                                           orange                                     770                 CH.sub.2CH.sub.2CH.sub.2OH                                                                   orange                                     __________________________________________________________________________    771                                                                                 ##STR344##    CH.sub.2CH.sub.2CH.sub.2OH                                                                   orange                                     __________________________________________________________________________    772                                                                                 ##STR345##    CH.sub.2CH.sub.2OH                                                                           yellowish red                              773                 CH.sub.2CH.sub. 2CH.sub. 2OH                                                                 yellowish  red                             __________________________________________________________________________    774                                                                                 ##STR346##    CH.sub. 2CH.sub.2CH.sub. 2OH                                                                 yellow                                     __________________________________________________________________________    775                                                                                 ##STR347##    CH.sub.2CH.sub.2OH                                                                           yellow                                     776                 CH.sub. 2CH.sub.2CH.sub. 2OH                                                                 yellow                                     777                 CH.sub.2CH.sub.2CH.sub.2CH.sub.3                                                             yellow                                     __________________________________________________________________________

EXAMPLE 778

19.5 parts of 3-amino-5-nitro-2,1-benzoisothiazole is added in portionswhile stirring at 15° to 25° C to about 75 to 85 parts of 96% sulfuricacid and the mixture is then cooled to 0° to 4° C. Then 32.5 parts of23% nitrosylsulfuric acid is dripped in at this temperature.Diazotization is ended after stirring for from about three to four hoursat 0° to 5° C. The diazonium salt mixture is then added to a solution orsuspension, cooled to 0° C, of 34.9 parts of the coupling component ofthe formula: ##STR348## in 50 parts of 30% hydrochloric acid, 500 partsof water and 150 parts of glacial acetic acid. During coupling, ice andsodium acetate are added at intervals so that the temperature of thecoupling mixture does not rise above 5° C and the pH is finally about 2.The precipitated dye of the formula: ##STR349## is filtered off, washedwith hot water and dried. About 53.6 parts of a black powder is obtainedwhich dissolves in dimethylformamide with a reddish blue color.

EXAMPLE 779

21.6 parts of 2-amino-5-nitrobenzenemethylsulfone-(1) is stirred at from10° to 15° C in 100 parts of 96% sulfuric acid. Then 32.5 parts of 23%nitrosylsulfuric acid is added at 0° to 5° C and the mixture is stirredfor four hours at 5° to 10° C. The diazonium salt solution obtained isallowed to flow within about twenty minutes into 35.5 parts of asuspension, cooled to 0° C, of the coupling component of the formula:##STR350## in a mixture of 100 parts of glacial acetic acid, 1 part ofsulamic acid, 30 parts by volume of concentrated hydrochloric acid and500 parts of water. During coupling the mixture is kept at pH 0 to 2 byadding sodium acetate, and water and ice are added for better stirring.

After coupling has ended (having proceeded at above pH 2) the dyemixture of the formulae: ##STR351## is suction filtered, washed withwater and dried. A dark powder is obtained which dissolves indimethylformamide with a reddish violet color and dyes polyethyleneterephthalate cloth reddish violet shades.

                                      TABLE 3                                     __________________________________________________________________________    Coupling component:                                                           __________________________________________________________________________     ##STR352##                                                                   __________________________________________________________________________    Example                                                                             Diazo component       R.sup.2           Shade                           __________________________________________________________________________    780                                                                                  ##STR353##           CH.sub.2CH.sub.2OH                                                                              yellowish red                   781                         CH.sub.2CH.sub.2CH.sub.2OH                                                                      yellowish red                   782                                                                                                        ##STR354##       yellowish red                   783                         CH.sub.2CH.sub.2CH.sub.2OCHO                                                                    yellowish red                   784   H                     yellowish red                                     785                         (CH.sub.2).sub.6OH                                                                              yellowish red                   786                         CH.sub.2CH.sub.2OCOCH.sub.3                                                                     yellowish                       __________________________________________________________________________                                                  red                             787                                                                                  ##STR355##           CH.sub.2CH.sub.2OH                                                                              yellowish red                   788                         CH.sub.2CH hd 2CH.sub.2OH                                                                       yellowish red                   789                                                                                                        ##STR356##       yellowish red                   790                         H                 yellowish                       __________________________________________________________________________                                                  red                             791                                                                                  ##STR357##           H                 red                             792                         CH.sub.2CH.sub.2OH                                                                              red                             793                         CH.sub.2CH hd 2CH.sub.2OH                                                                       red                             794                                                                                                        ##STR358##       red                             795                         CH.sub.2CH.sub.2OCH.sub.3                                                                       red                             796                         CH.sub.2CH.sub.2CH.sub.2OCH.sub.3                                                               red                             797                         CH.sub.2CH.sub.2OCOCH.sub.3                                                                     red                             __________________________________________________________________________    798                                                                                  ##STR359##           H                 red                             799                         CH.sub.2CH.sub.2OH                                                                              red                             800                         CH.sub.2CH.sub.2CH.sub.2OH                                                                      red                             801                                                                                                        ##STR360##       red                             __________________________________________________________________________    802                                                                                  ##STR361##            CH.sub.2CH.sub.2OCH.sub.3                                                                      red                             803                         C.sub.2 H.sub.5   red                             __________________________________________________________________________    804                                                                                  ##STR362##           CH.sub.2CH.sub.2OH                                                                              red                             805                         CH.sub.2CH.sub.2CH.sub.2OH                                                                      red                             __________________________________________________________________________    806                                                                                  ##STR363##           CH.sub.2CH.sub.2OH                                                                              red                             807                         CH.sub.2CH.sub.2CH.sub.2OH                                                                      red                             __________________________________________________________________________    808                                                                                  ##STR364##           CH.sub.2CH.sub.2OH                                                                              red                             809                         CH.sub.2CH.sub.2CH.sub.2OH                                                                      red                             __________________________________________________________________________    810                                                                                  ##STR365##           H                 red                             811                         CH.sub.2CH.sub.2OH                                                                              red                             812                         CH.sub.2CH.sub.2CH.sub.2OH                                                                      red                             813                         CH.sub.2CH.sub.2OCH.sub.3                                                                       red                             __________________________________________________________________________    814                                                                                  ##STR366##           CH.sub.2CH.sub.2OH                                                                              yellowish red                   815                         CH.sub.2CH.sub.2CH.sub.2OH                                                                      yellowish red                   816                         CH.sub.2CH.sub.2OCOCH.sub.3                                                                     yellowish                       __________________________________________________________________________                                                  red                             817                                                                                  ##STR367##           CH.sub.2CH.sub.2CH.sub.2OH                                                                      yellowish red                   818                         CH.sub.2CH.sub.2CH.sub.2OH                                                                      yellowish                       __________________________________________________________________________                                                  red                             819                                                                                                        ##STR368##       yellowish                       __________________________________________________________________________                                                  red                             820                                                                                  ##STR369##           CH.sub.2CH.sub.2OH                                                                              yellowish red                   821                         CH.sub.2CH.sub.2CH.sub.2OH                                                                      yellowish red                   822                         CH.sub.2CH.sub.2CH.sub.2OCH hd                                                                  yellowish                       __________________________________________________________________________                                                  red                             823                                                                                  ##STR370##           CH.sub.2CH.sub.2OH                                                                              bluish red                      864                         CH.sub.2CH.sub.2CH.sub.2OH                                                                      orange                          __________________________________________________________________________    865                                                                                  ##STR371##           CH.sub.2CH.sub.2OH                                                                              orange                          866                         CH.sub.2CH.sub.2CH.sub.2OH                                                                      orange                          867                                                                                                        ##STR372##       orange                          868   H                     orange                                            __________________________________________________________________________    869                                                                                  ##STR373##           CH.sub.2CH.sub.2OH                                                                              violet                          870                         CH.sub.2CH.sub.2CH.sub.2OCH.sub.3                                                               violet                          __________________________________________________________________________    871                                                                                  ##STR374##           CH.sub.2CH.sub.2OH                                                                              bluish red                      872                         CH.sub.2CH.sub.2CH.sub.2OH                                                                      bluis red                       873                                                                                                        ##STR375##       bluish red                      __________________________________________________________________________    874                                                                                  ##STR376##           CH.sub.2CH.sub.2OH                                                                              bluish red                      875                         CH.sub.2CH.sub.2CH.sub. 2OH                                                                     bluish red                      __________________________________________________________________________    876                                                                                  ##STR377##           CH.sub.2CH.sub.2CH.sub.2OH                                                                      yellowish                       __________________________________________________________________________                                                  red                             877                                                                                  ##STR378##           CH.sub.2CH.sub.2OH                                                                              bluish red                      878                         CH.sub.2CH.sub.2CH.sub.2OH                                                                      bluish red                      879                         H                 bluish red                      __________________________________________________________________________    880                                                                                  ##STR379##           CH.sub.2CH.sub.2OH                                                                              violet                          881                         CH.sub.2CH.sub.2CH.sub.2OH                                                                      violet                          __________________________________________________________________________    882                                                                                  ##STR380##           CH.sub.2CH.sub.2CH.sub.2OH                                                                      blue                            __________________________________________________________________________

                                      TABLE 4                                     __________________________________________________________________________                ##STR381##                                                        Coupling component:                                                           Example                                                                            Diazo component  R.sup.1             Shade                               __________________________________________________________________________    883                                                                                 ##STR382##      CH.sub.2CH.sub.2OH  yellowish red                       884                   CH.sub.2CH.sub.2CH.sub.2OH                                                                        "                                   __________________________________________________________________________    885                                                                                 ##STR383##      H                   yellowish red                       886                   CH.sub.2CH.sub.2OH  "                                   887                   CH.sub.2CH.sub.2OCOCH.sub.3                                                                       "                                   888                   CH.sub.2CH.sub.2CH.sub.2OH                                                                        "                                   889                   CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCHO                                                             "                                   890                   (CH.sub.2).sub.6 OH "                                   __________________________________________________________________________    891                                                                                 ##STR384##      CH.sub.2CH.sub.2CH.sub.2OH                                                                        red                                 892                   CH.sub.2CH.sub.2OH  "                                   __________________________________________________________________________    893                                                                                 ##STR385##      H                   red                                 894                   CH.sub.2CH.sub.2OH  "                                   895                   CH.sub.2CH.sub.2CH.sub.2OH                                                                        "                                   __________________________________________________________________________    896                                                                                 ##STR386##      H                   red                                 897                   CH.sub.2CH.sub.2OH  "                                   898                   CH.sub.2CH.sub.2CH.sub.2OH                                                                        "                                   __________________________________________________________________________    899                                                                                 ##STR387##      CH.sub.2CH.sub.2CH.sub.2OH                                                                        violet                              __________________________________________________________________________    900                                                                                 ##STR388##      CH.sub.2CH.sub. 2CH.sub.2OH                                                                       red                                 __________________________________________________________________________    901                                                                                 ##STR389##      CH.sub.2CH.sub.2CH.sub.2OH                                                                        violet                              __________________________________________________________________________    902                                                                                 ##STR390##      CH.sub.2CH.sub.2CH.sub.2OH                                                                        reddish blue                        __________________________________________________________________________    903                                                                                 ##STR391##      H                   red                                 904                   CH.sub.2CH.sub.2OH  "                                   905                   CH.sub.2CH.sub.2CH.sub.2OH                                                                        "                                   __________________________________________________________________________    906                                                                                 ##STR392##      CH.sub.2CH.sub.2CH.sub.2OH                                                                        bluish red                          __________________________________________________________________________    907                                                                                 ##STR393##      CH.sub.2CH.sub.2CH.sub.2OH                                                                        bluish red                          __________________________________________________________________________    908                                                                                 ##STR394##      CH.sub.2CH.sub.2CH.sub.2OH                                                                        red                                 __________________________________________________________________________

                                      TABLE 5                                     __________________________________________________________________________                ##STR395##                                                        Coupling component:                                                           Example                                                                            Diazo component  R.sup.2           Shade                                 __________________________________________________________________________    909                                                                                 ##STR396##      CH.sub.2CH.sub.2OH  red                                 910                   CH.sub.2CH.sub.2CH.sub.2OCH.sub.3                                                                 "                                   911                   CH.sub.2CH.sub.2CH.sub.2OH                                                                        "                                   912                   CH.sub.2CH.sub.2OCH.sub.3                                                                         "                                   __________________________________________________________________________    913                                                                                 ##STR397##      CH.sub.2CH.sub.2OH  bluish red                          914                   CH.sub.2CH.sub.2CH.sub.2OH                                                                        "                                   915                   CH.sub.2CH.sub.2C.sub.6 H.sub.5                                                                   "                                   916                   CH.sub.2CH.sub.2CH.sub.2OCH.sub.3                                                                 "                                   917                   C.sub.2 H.sub.5     "                                   918                                                                                 ##STR398##      CH.sub.2CH.sub.2OH  red violet                          919                   (CH.sub.2).sub.3OH  "                                   920                   C.sub.2 H.sub.4 OCH.sub.3                                                                         "                                   921                   C.sub.2 H.sub.5     "                                   __________________________________________________________________________    922                                                                                 ##STR399##      CH.sub.2CH.sub.2OH  red violet                          923                   (CH.sub.2).sub.3OH  "                                   924                   C.sub.2 H.sub.5     "                                   __________________________________________________________________________    925                                                                                 ##STR400##      (CH.sub.2).sub.3OH  blue                                926                   C.sub.3 H.sub.6OCH.sub.3                                                                          "                                   __________________________________________________________________________    927                                                                                 ##STR401##      (CH.sub.2).sub.3OH  yellowish red                       928                   CH.sub.2CH.sub.2CH.sub.2OCH.sub.3                                                                 "                                   929                   C.sub.3 H.sub.7 (n) "                                   __________________________________________________________________________    930                                                                                 ##STR402##      CH.sub.2CH.sub.2OH  yellowish red                       931                   (CH.sub.2).sub.3OH  "                                   932                   C.sub.6 H.sub.5     red                                 __________________________________________________________________________    933                                                                                 ##STR403##      CH.sub.2CH.sub.2OH  orange                              934                   CH.sub.2CH.sub.2CH.sub.2OH                                                                        "                                   __________________________________________________________________________

                                      table 6                                     __________________________________________________________________________                  ##STR404##                                                      coupling component:                                                           Example                                                                            Diazo component R.sup.2        Shade                                     __________________________________________________________________________    935                                                                                  ##STR405##    CH.sub.2CH.sub.2C.sub.6 H.sub.5                                                              yellowish red                             936                  CH.sub.2CH.sub.2OH                                                                           red                                       937                  CH.sub.2CH.sub.2CH.sub.2OH                                                                   "                                         938                                                                                                 ##STR406##    yellowish red                             939                                                                                  ##STR407##    CH.sub.2CH.sub.2C.sub.6 H.sub.5                                                              yellowish red                             940                  CH.sub.2CH.sub.2OH                                                                           "                                         941                  CH.sub.2CH.sub.2CH.sub.2OH                                                                   "                                         __________________________________________________________________________    942                                                                                  ##STR408##    CH.sub.2CH.sub.2C.sub.6 H.sub.5                                                              orange                                    943                  CH.sub.2CH.sub.2OH                                                                           "                                         944                  CH.sub.2CH.sub.2CH.sub.2OH                                                                   "                                         __________________________________________________________________________    945                                                                                  ##STR409##    C.sub.4 H.sub.9 (n)                                                                          bluish red                                946                  CH.sub.2CH.sub.2OH                                                                           red                                       947                  CH.sub.2CH.sub.2CH.sub.2OH                                                                   "                                         __________________________________________________________________________    948                                                                                  ##STR410##    C.sub.4 H.sub.9 (n)                                                                          red                                       949                  CH.sub.2CH.sub.2OH                                                                           "                                         950                  CH.sub.2CH.sub.2CH.sub.2OH                                                                   "                                         __________________________________________________________________________    951                                                                                  ##STR411##    CH.sub.2CH.sub.2C.sub.6 H.sub.5                                                              yellow                                    952                  CH.sub.2CH.sub.2OH                                                                           "                                         __________________________________________________________________________

example 953

20 parts of the dye of the formula: ##STR412## is stirred with 100 partsof formic acid for ten hours at 80° to 100° C. About 50 parts of formicacid is then distilled off at subatmospheric pressure and the residue iscooled and iluted with 500 parts by volume of water. The precipitateddye of the formula: ##STR413## is filtered off, washed with water anddried. It dissolves in dimethylformamide with an orange color and dyespolyethylene terephthalate cloth full orange shades of excellent lightfastness.

The following dyes are also valuable:

    __________________________________________________________________________    954                                                                                ##STR414##                           orange                              __________________________________________________________________________    955                                                                                ##STR415##                           yellowish red                       __________________________________________________________________________    956                                                                                ##STR416##                           yellow                              __________________________________________________________________________    957                                                                                ##STR417##                           orange                              __________________________________________________________________________    958                                                                                ##STR418##                           reddish violet                      __________________________________________________________________________    959                                                                                ##STR419##                           yellow                              __________________________________________________________________________    960                                                                                ##STR420##                           yellowish red                       __________________________________________________________________________    961                                                                                ##STR421##                           yellow                              __________________________________________________________________________

EXAMPLE 962

A mixture of 56 parts of 2,6-dichloro-3-cyano-4-methylpyridine, 160parts by volume of N-methylpyrrolidone and 50 parts by volume oftriethylamine has 50 parts of the amine of the formula: ##STR422## addedto it. The mixture is stirred for about ten hours at 55° to 60° C, thenabout 1000 parts of water is added and the mixture is acidified withconcentrated hydrochloric acid. A red brown oil separates and isisolated after decantation of the aqueous phase and washing with water.About 60 parts of 2-hydroxyethylamine is then added and the mixture isstirred for from three to four hours at 105° to 130° C. After coolingthe whole is diluted with about 300 parts of glacial acetic acid andacidified with 50 parts by volume of concentrated hydrochloric acid. Iceis added to the mixture until it has been cooled to 0° C and then thereis added a diazonium salt solution which has been prepared as follows:49 parts of 2-amino-5-nitrobenzonitrile is added at 0° at 4° C inportions while stirring well to a mixture of 240 parts of concentratedsulfuric acid and 98 parts of 23% nitrosylsulfuric acid. The mixture isstirred for from four to five hours at 0° to 4° C and is then added inportions to the coupling mixture described above. The mixture is keptstirrable and the temperature is kept at not more than 0° C by thesimultaneous addition of ice and ice-water. Aqueous sodium acetatesolution is then added over twenty minutes until the pH of the couplingmixture is from 1.5 to 1.0. After coupling is over the mixture is heatedto 60° to 80° C, and the precipitated dye is suction filtered, washedwith water and dried. About 152 parts of a reddish brown powder isobtained which dissolves in dimethylformamide with a red color and dyespolyethylene terephthalate cloth red shades of excellent fastness tolight, wet treatment and dry-heat pleating and setting.

The dye has the formula: ##STR423## and contains a minor amount of the2,6-dialkylaminopyridine isomer of the formula: ##STR424##

Dyes characterized in the following Tables by specifying the diazo andcoupling components are obtained analogously:

                                      TABLE 1                                     __________________________________________________________________________                ##STR425##                                                        Coupling component:                                                           Example                                                                            Diazo component          R.sup.2             Shade                       __________________________________________________________________________    963                                                                                 ##STR426##              H                   yellow                      964                           CH.sub.2CH.sub.2OH  "                           965                           CH.sub.2CH.sub.2OH  "                           966                           CH.sub.2CHOH        "                                                         CH.sub.3                                        967                           CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                               "                           968                           CH.sub.2CH.sub.2OCH.sub.3                                                                         "                           969                                                                                 ##STR427##              H                   yellow                      970                           CH.sub.2CH.sub.2OH  "                           971                           CH.sub.2CH.sub.2CH.sub.2OH                                                                        "                           972                                                                                                          ##STR428##         "                           973                           CH.sub.2CH.sub.2OCH.sub.2OH                                                                       "                           974                                                                                 ##STR429##              H                   "                           975                           CH.sub.2CH.sub.2CH  "                           976                           CH.sub.2CH.sub.2CH.sub.2OH                                                                        "                           977                                                                                                          ##STR430##         "                           978                           CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                               "                           979                                                                                 ##STR431##              H                   "                           980                           CH.sub.2CH.sub.2OH  "                           981                           CH.sub.2CH.sub.2CH.sub.2OH                                                                        "                           982                                                                                                          ##STR432##         "                           982 a)                        CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                               "                           983                                                                                 ##STR433##              H                   orange                      984                           CH.sub.2CH.sub.2OH                              985                           CH.sub.2CH.sub.2CH.sub.2OH                      986                                                                                                          ##STR434##                                     987                           CH.sub.2CH.sub.2 OCH.sub.2CH.sub.2OH            988                                                                                 ##STR435##              H                   orange                      989                           CH.sub.2CH.sub.2OH                              990                           CH.sub.2CH.sub.2CH.sub.2OH                      991                           CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH             992                                                                                 ##STR436##              H                   orange                      993                           CH.sub.2CH.sub.2OH                              994                           CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3             995                                                                                                          ##STR437##                                     996                                                                                 ##STR438##              CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                               orange                      997                           CH.sub.2CH.sub.2OCH.sub.3                       998                           CH.sub.2CH.sub.2CH.sub.2OCH.sub.3               999                           CH.sub.2CH.sub.2 OCHO                           1000                          (CH.sub.2).sub.6OH                              1001                                                                                ##STR439##              H                   yellowish red               1002                           CH.sub.2CH.sub.2OH                             1003                          CH.sub.2CH.sub.2CH.sub.2OH                      1004                          CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH             1005                                                                                                         ##STR440##                                     1006                          CH.sub.2CH.sub.2CH.sub.2OCH.sub.3               1007                          CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3             1008                                                                                ##STR441##              CH.sub.2CH.sub.2OH  yellowish red               1009                          CH.sub.2CH.sub.2CH.sub.2OH                      1010                          CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH             1011                                                                                ##STR442##              CH.sub.2CH.sub.2OH  yellowish red               1012                          CH.sub.2CH.sub.2CH.sub.2OH                      1013                          CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH             1014                                                                                ##STR443##              CH.sub.2CH.sub.2OH  orange                      1015                          CH.sub.2CH.sub.2CH.sub.2OH                      1016                                                                                ##STR444##              CH.sub.2CH.sub.2OH  yellow                      1017                          CH.sub.2CH.sub.2CH.sub.2OH                      1018                          CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH             1019                                                                                ##STR445##              CH.sub.2CH.sub.2OH  orange                      1020                          CH.sub.2CH.sub.2CH.sub.2OH                      1021                          CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH             1022                                                                                ##STR446##              CH.sub.2CH.sub.2OH  yellow                      1023                          CH.sub.2CH.sub.2CH.sub.2OH                      1024                          CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH             1025                                                                                ##STR447##              H                   yellow                      1026                          CH.sub.2CH.sub.2OH                              1027                          CH.sub.2CH.sub.2CH.sub.2OH                      1028                          CH.sub.2CH.sub.2CH.sub.2OCH.sub.3               1029                                                                                ##STR448##              CH.sub.2CH.sub.2OH  yellow                      1030                          CH.sub.2CH.sub.2CH.sub.2OH                      1031                          CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH             1032                                                                                ##STR449##              H                   yellow                      1033                          CH.sub.2CH.sub.2OH                              1034                          CH.sub.2CH.sub.2CH.sub.2OH                      1035                          CH.sub.2CH.sub.2OCH.sub.2OH                     1036                          CH.sub.2CH.sub.2OCH.sub.3                       1037                                                                                ##STR450##              CH.sub.2CH.sub.2CH.sub.2OH                                                                        yellowish red               1038                          CH.sub.2CH.sub.2OH                              1039                                                                                ##STR451##              CH.sub.2CH.sub.2CH.sub.2OH                                                                        orange                      1040                          CH.sub.2CH.sub.2OCH.sub.2CH.sub. 2OH            1041                                                                                ##STR452##              CH.sub.2CH.sub.2OH  yellow                      1042                          CH.sub.2CH.sub.2CH.sub.2OH                      1043                          CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH             1044                                                                                ##STR453##              CH.sub.2CH.sub.2OH  yellow                      1045                          CH.sub.2CH.sub.2CH.sub.2OH                      1046                                                                                                         ##STR454##                                     1047                          CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH             1048                                                                                ##STR455##              CH.sub.2CH.sub.2OH  yellow                      1049                          CH.sub.2CH.sub.2CH.sub.2OH                      1050                          CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH             1051                                                                                ##STR456##              CH.sub. 2CH.sub.2OH yellow                      1052                          CH.sub.2CH.sub.2CH.sub.2OH                      1053                                                                                ##STR457##              CH.sub.2CH.sub.2OH  yellow                      1054                          CH.sub.2CH.sub.2CH.sub.2OH                      __________________________________________________________________________

                                      table 2                                     __________________________________________________________________________                   ##STR458##                                                     coupling component                                                            Example                                                                            Diazo component                                                                              R.sup.1             Shade                                 __________________________________________________________________________    1055                                                                                ##STR459##    CH.sub.2CH.sub.2OH  yellow                                1056                CH.sub.2CH.sub.2CH.sub. 2OH                               __________________________________________________________________________    1057                                                                                ##STR460##    H                   yellow                                1058                CH.sub.2CH.sub.2OH                                        1059                CH.sub.2CH.sub.2CH.sub.2OH                                1060                CH.sub.2CH.sub.2CH.sub.2O(CH.sub.2).sub.2 OH              __________________________________________________________________________    1061                                                                                ##STR461##    CH.sub.2CH.sub.2OH  yellow                                1062                CH.sub.2CH.sub.2CH.sub.2OH                                1063                CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                       __________________________________________________________________________    1064                                                                                ##STR462##    CH.sub.2CH.sub.2OH  orange                                1065                CH.sub.2CH.sub.2CH.sub.2OH                                1066                CH.sub.2CH.sub.2O(CH.sub.2).sub.2 OH                      __________________________________________________________________________    1067                                                                                ##STR463##    CH.sub.2CH.sub.2CH.sub.2OH                                                                        orange                                1068                CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                       __________________________________________________________________________    1069                                                                                ##STR464##    CH.sub.2CH.sub.2OH  scarlet                               1070                CH.sub.2CH.sub.2CH.sub.2OH                                __________________________________________________________________________    1071                                                                                ##STR465##    CH.sub.2CH.sub.2CH.sub.2OH                                                                        yellow                                1072                CH.sub.2CH.sub.2O(CH.sub.2).sub.2 OH                      __________________________________________________________________________    1073                                                                                ##STR466##    CH.sub.2CH.sub.2OH  yellow                                1074                CH.sub.2CH.sub.2CH.sub.2OH                                1075                CH.sub.2CH.sub.2CH.sub.2CH.sub.3                          __________________________________________________________________________

example 1076

19.5 parts of 3-amino-5-nitro-2,1-benzoisothazole is added whilestirring at 15° to 25° C in portions to about 75 to 85 parts of 96%sulfuric acid and the mixture is cooled to 0° to 4° C. 32.5 parts of 23%nitrosylsulfuric acid is then dripped in at this temperature.Diazotization is over after from about three to four hours' stirring at0° to 5° C. The diazonium salt mixture is added to a solution orsuspension of 34 parts of the coupling component of the formula:##STR467## in 50 parts of 30% hydrochloric acid, 500 parts of water and150 parts of glacial acetic acid. During coupling ice and sodium acetateare added at intervals so that the temperature of the coupling mixturedoes not rise above 5° C and the pH is finally about 2. The precipitateddye of the formula: ##STR468## is filtered off, washed with hot waterand dried. About 33 parts of a black powder is obtained which dissolvesin dimethylformamide with a reddish blue color and dyes polyethyleneterephthalate cloth reddish blue shades having very good fastnessproperties.

EXAMPLE 1077

11 parts of 2-amino-5-nitrobenzoic acid methoxyethyl ester has 180 partsby volume of glacial acetic acid, 15 parts by volume of concentratedhydrochloric acid and 10 parts of ice added to it. The whole is cooledto 0° to 5° C and then 13.5 parts by volume of 23% sodium nitritesolution is added. After stirring for from about two to three hours anyexcess of nitrous acid present is destroyed in the usual way, thediazonium salt solution is diluted with 1000 party by volume ofice-water and then a solution of 11.9 parts of the coupling component ofthe formula: ##STR469## in 100 parts of glacial acetic acid and 10 partsof concentrated hydrochloric acid is added. The whole is stirred forhalf an hour and then 50% caustic soda solution is adde until the pH ofthe coupling mixture is 2. After coupling is over the precipitated dyeof the formula: ##STR470## is filtered off, washed with water and dried.

A red powder is obtained which dissolves in dimethylformamide with a redcolor and dyes polyethylene terephthalate full yellowish red shadeshaving very good fastness properties.

                                      TABLE 3                                     __________________________________________________________________________                         ##STR471##                                               Coupling component:                                                           Example                                                                            Diazo component       R.sup.2               Shade                        __________________________________________________________________________    1078                                                                                ##STR472##           CH.sub.2CH.sub.3                                   1079                       CH.sub.2CH.sub.2CH.sub.2OH                         1080                                                                                                      ##STR473##                                        1081                       CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                1082                       CH.sub.2CH.sub.2CH.sub.2OCH.sub.3                  1083                       H                                                  1084                       (CH.sub.2).sub.6OH                                 1085                       CH.sub.2CH.sub.2OCOCH.sub.3                        __________________________________________________________________________    1086                                                                                ##STR474##           CH.sub.2CH.sub.2OH                                 1087                       CH.sub.2CH.sub.2CH.sub.2OH                         1088                                                                                                      ##STR475##                                        1089                       CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                1090                       H                                                  __________________________________________________________________________    1091                                                                                ##STR476##           H                                                  1092                       CH.sub.2CH.sub.2OH                                 1093                       CH.sub.2CH.sub.2CH.sub.2OH                         1094                                                                                                      ##STR477##                                        1095                       CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                1096                       CH.sub.2CH.sub.2OCH.sub.3                          1097                       CH.sub.2CH.sub.2CH.sub.2OCH.sub.3                  1098                       CH.sub.2CH.sub.2OCOCH.sub.3                        __________________________________________________________________________    1099                                                                                ##STR478##           H                     red                          1100                       CH.sub.2CH.sub.2OH                                 1101                       CH.sub.2CH.sub.2CH.sub.2OH                         1102                                                                                                      ##STR479##                                        1103                       CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                1104                       CH.sub.2CH.sub.2OCH.sub.3                          1105                       C.sub.2 H.sub.5                                    __________________________________________________________________________    1106                                                                                ##STR480##           CH.sub.2CH.sub.2OH    red                          1107                       CH.sub.2CH.sub.2CH.sub.2OH                         1108                       CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                __________________________________________________________________________    1109                                                                                ##STR481##           CH.sub.2CH.sub.2OH    red                          1110                       CH.sub.2CH.sub.2CH.sub.2OH                         1111                       CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                __________________________________________________________________________    1112                                                                                ##STR482##           CH.sub.2CH.sub.2OH    red                          1113                       CH.sub.2CH.sub.2CH.sub.2OH                         __________________________________________________________________________    1114                                                                                ##STR483##           H                     red                          1115                       CH.sub.2CH.sub.2OH                                 1116                       CH.sub.2CH.sub.2CH.sub.2OH                         1117                       CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                1118                       CH.sub.2CH.sub.2OCH.sub.3                          __________________________________________________________________________    1119                                                                                ##STR484##           CH.sub.2CH.sub.2OH    yellowish red                1120                       CH.sub.2CH.sub.2CH.sub.2OH                         1121                       CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                1122                       CH.sub.2CH.sub.2OCH.sub.3                          __________________________________________________________________________    1123                                                                                ##STR485##           CH.sub.2CH.sub.2OH    yellowish red                1124                       CH.sub.2CH.sub.2CH.sub.2OH                         1125                                                                                                      ##STR486##                                        1126                       CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                __________________________________________________________________________    1127                                                                                ##STR487##           CH.sub.2CH.sub.2OH    yellowish red                1128                       CH.sub.2CH.sub.2CH.sub.2OH                         1129                       CH.sub.2CH.sub.2CH.sub.2OCH.sub.3                  __________________________________________________________________________    1130                                                                                ##STR488##           CH.sub.2CH.sub.2OH    bluish red                   1131                       CH.sub.2CH.sub.2CH.sub.2OH                         1132                       CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                1133                       CH.sub.2CH.sub.2CH.sub.2OCH.sub.3                  __________________________________________________________________________    1134                                                                                ##STR489##           CH.sub.2CH.sub.2OH    red                          1135                       CH.sub.2CH.sub.2CH.sub.2OH                         __________________________________________________________________________    1136                                                                                ##STR490##           CH.sub.2CH.sub.2OH    red                          1137                       CH.sub.2CH.sub.2CH.sub.2OH                         1138                       CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                __________________________________________________________________________    1139                                                                                ##STR491##           CH.sub.2CH.sub.2OH    yellow                       1140                       CH.sub.2CH.sub.2CH.sub.2OH                         1141                       CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                __________________________________________________________________________    1142                                                                                ##STR492##           CH.sub.2CH.sub.2OH    yellow                       1143                       CH.sub.2CH.sub.2CH.sub.2OH                         1144                       CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                __________________________________________________________________________    1145                                                                                ##STR493##           H                     red                          1146                       CH.sub.2CH.sub.2OH                                 1147                       CH.sub.2CH.sub.2CH.sub.2OH                         1148                                                                                                      ##STR494##                                        1149                       (CH.sub.2).sub.3O(CH.sub.2).sub.4OH                __________________________________________________________________________    1150                                                                                ##STR495##           CH.sub.2CH.sub.2OH    reddish blue                 1151                       CH.sub.2CH.sub.2CH.sub.2OH                         1152                                                                                                      ##STR496##                                        1153                       CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                1154                       (CH.sub.2).sub.6OH                                 1155                       (CH.sub.2).sub.3O(CH.sub.2).sub.4OH                1156                                                                                                      ##STR497##                                        __________________________________________________________________________    1157                                                                                ##STR498##           CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                 blue                         __________________________________________________________________________    1158                                                                                ##STR499##           CH.sub.2CH.sub.2CH.sub.2OH                                                                          yellowish brown              1159                       CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                __________________________________________________________________________    1160                                                                                ##STR500##           CH.sub.2CH.sub.2CH.sub.2OH                                                                          yellow                       1161                       CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                __________________________________________________________________________    1162                                                                                ##STR501##           CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                 yellow                       1163                       (CH.sub.2).sub.3OH                                 __________________________________________________________________________    1164                                                                                ##STR502##           CH.sub.2CH.sub.2OH    bluish red                   1165                       CH.sub.2CH.sub.2CH.sub.2OH                         1166                       H                                                  1167                       CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                __________________________________________________________________________    1168                                                                                ##STR503##           (CH.sub.2).sub.3 3OH  bluish red                   1169                       CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                1170                       H                                                  __________________________________________________________________________    1171                                                                                ##STR504##           CH.sub.2CH.sub.2OH    yellowish                    __________________________________________________________________________                                                     red                          1172                                                                                ##STR505##           CH.sub.2CH.sub.2CH.sub.2OH                                                                          scarlet                      1173                       CH.sub.2CH.sub.2OH                                 __________________________________________________________________________    1174                                                                                ##STR506##           CH.sub.2CH.sub.2OH    scarlet                      1175                                                                                ##STR507##           H                     bluish red                   1176                       CH.sub.2CH.sub.2OH                                 1177                       CH.sub.2CH.sub.2CH.sub.2OH                         1178                       CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                1179                       (CH.sub.2).sub.3O(CH.sub.2).sub.4OH                __________________________________________________________________________    1180                                                                                ##STR508##           CH.sub.2CH.sub.2CH.sub.2OH                                                                          violet                       1181                       CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                 violet                       1182                       H                     bluish                       __________________________________________________________________________                                                     red                          1183                                                                                ##STR509##           CH.sub.2CH.sub.2CH.sub.2OH                                                                          violet                       1184                       CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                __________________________________________________________________________    1185                                                                                ##STR510##           CH.sub.2CH.sub.2CH.sub.2OH                         __________________________________________________________________________    1186                       CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                1187                                                                                ##STR511##           CH.sub.2CH.sub.2CH.sub.2OH                                                                          red                          __________________________________________________________________________    1188                                                                                ##STR512##           H                     orange                       1189                       CH.sub.2CH.sub.2OH                                 1190                       CH.sub.2CH.sub.2CH.sub.2OH                         1191                       CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                __________________________________________________________________________    1192                                                                                ##STR513##           CH.sub.2CH.sub.3      orange                       1193                       CH.sub.2CH.sub.2CH.sub.2OH                         1194                                                                                                      ##STR514##                                        1195                       CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                1196                       H                                                  __________________________________________________________________________    1197                                                                                ##STR515##           CH.sub.2CH.sub.2OH                                 1198                       CH.sub.2CH.sub.2CH.sub.2OH                         1199                       CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                __________________________________________________________________________    1200                                                                                ##STR516##           CH.sub.2CH.sub.2OH    bluishred                    1201                       CH.sub.2CH.sub.2CH.sub.2OH                         1202                       CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                1203                                                                                                      ##STR517##                                        __________________________________________________________________________    1204                                                                                ##STR518##           CH.sub.2CH.sub.2OH    bluish red                   1205                       CH.sub.2CH.sub.2CH.sub.2OH                         1206                       CH.sub.2 CH.sub.2OCH.sub.2CH.sub.2OH               __________________________________________________________________________    1207                                                                                ##STR519##           CH.sub.2CH.sub.2CH.sub.2OH                                                                          yellowish                    __________________________________________________________________________                                                     red                          1208                                                                                ##STR520##           CH.sub.2CH.sub.2OH    bluish red                   1209                       CH.sub.2CH.sub.2CH.sub.2OH                         1210                       H                                                  __________________________________________________________________________    1211                                                                                ##STR521##           CH.sub.2CH.sub.2OH    violet                       1212                       CH.sub.2CH.sub.2CH.sub.2OH                         __________________________________________________________________________    1213                                                                                ##STR522##           CH.sub.2CH.sub.2CH.sub.2OH                                                                          reddish                      __________________________________________________________________________                                                     blue                     

                                      TABLE 4                                     __________________________________________________________________________    Coupling component:                                                            ##STR523##                                                                   Example                                                                             Diazo component     R.sup.2             Shade                           __________________________________________________________________________    1214                                                                                 ##STR524##         CH.sub.2CH.sub.2OH  yellowish red                   1215                      CH.sub.2CH.sub.2CH.sub.2OH                          1216                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                 __________________________________________________________________________    1217                                                                                 ##STR525##         H                   yellowish red                   1218                      CH.sub.2CH.sub.2OH                                  1219                      CH.sub.2CH.sub.2OCOCH.sub.3                         1220                      CH.sub.2CH.sub.2CH.sub.2OH                          1221                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                 1222                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCHO               1223                      (CH.sub.2).sub.6 OH                                 __________________________________________________________________________    1224                                                                                 ##STR526##         CH.sub.2CH.sub.2CH.sub.2OH                                                                        red                             1225                      CH.sub.2CH.sub.2OH                                  __________________________________________________________________________    1226                                                                                 ##STR527##         H                                                   1227                      CH.sub.2CH.sub.2OH                                  1228                      CH.sub.2CH.sub.2CH.sub.2OH                          1229                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                 __________________________________________________________________________    1230                                                                                 ##STR528##         H                   red                             1231                      CH.sub.2CH.sub.2OH                                  1232                      CH.sub.2CH.sub.2CH.sub.2OH                          1233                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                 1234                      (CH.sub.2).sub.3O(CH.sub.2).sub.4OH                 __________________________________________________________________________    1235                                                                                 ##STR529##         CH.sub.2CH.sub.2CH.sub.2OH                                                                        violet                          __________________________________________________________________________    1236                                                                                 ##STR530##         CH.sub.2CH.sub.2CH.sub.2OH                          1237                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                 __________________________________________________________________________    1238                                                                                 ##STR531##         CH.sub.2CH.sub.2CH.sub.2OH                                                                        violet                          1239                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                 __________________________________________________________________________    1240                                                                                 ##STR532##         CH.sub.2CH.sub.2CH.sub.2OH                                                                        reddish blue                    1241                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                 __________________________________________________________________________    1242                                                                                 ##STR533##         CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                               blue                            __________________________________________________________________________    1243                                                                                 ##STR534##         H                   red                             1244                      CH.sub.2CH.sub.2OH                                  1245                      CH.sub.2CH.sub.2CH.sub.2OH                          1246                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                 __________________________________________________________________________    1247                                                                                 ##STR535##         CH.sub.2CH.sub.2CH.sub.2OH                                                                        bluish red                      1248                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                 __________________________________________________________________________    1249                                                                                 ##STR536##         CH.sub.2CH.sub.2CH.sub.2OH                                                                        bluish red                      1250                      CH.sub.2CH.sub.2O(CH.sub.2).sub.2 OH                __________________________________________________________________________    1251                                                                                 ##STR537##         CH.sub.2CH.sub.2CH.sub.2OH                                                                        red                             1252                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                 __________________________________________________________________________

                                      table 5                                     __________________________________________________________________________    dye:                                                                           ##STR538##                                                                   No. Y       Y.sup.1                                                                             Y.sup.2                                                                             E      Shade                                          __________________________________________________________________________    1345                                                                              Cl      NO.sub.2                                                                            H     CH.sub.3                                                                             yellowish red                                  1346                                                                              Cl      Cl    CN    CH.sub.3                                                                             orange                                         1347                                                                              CN      Br    H     CH.sub.3                                                                             yellow                                         1348                                                                              CH.sub.3                                                                              NO.sub.2                                                                            H     CH.sub.3                                                                             orange                                         1349                                                                              OCH.sub.3                                                                             NO.sub.2                                                                            H     CH.sub.3                                                                             yellowish red                                  1350                                                                              SO.sub.2 CH.sub.3                                                                     NO.sub.2                                                                            H     CH.sub.3                                                                             bluish red                                     1351                                                                              CF.sub.3                                                                              H     H     CH.sub.3                                                                             yellow                                         1352                                                                              CF.sub.3                                                                              Cl    H     CH.sub.3                                                                             yellow                                         1353                                                                              CN      CN    H     CH.sub.3                                                                             orange                                         1354                                                                              H       NO.sub.2                                                                            H     C.sub.2 H.sub.5                                                                      orange                                         1355                                                                              H       NO.sub.2                                                                            H     C.sub.3 H.sub.7 (n)                                                                  orange                                         __________________________________________________________________________

                                      TABLE 6                                     __________________________________________________________________________    Coupling component:                                                            ##STR539##                                                                   No. Diazo component                                                                             R.sup.2      B     B.sup.1                                                                            Shade                               __________________________________________________________________________    1269                                                                               ##STR540##   CH.sub.2CH.sub.2OH                                                                         CH.sub.3                                                                            H    reddish violet                      1270              CH.sub.2CH.sub.2OH                                                                         H     CH.sub.2                                                                           reddish                                                                  violet                                   1271              CH.sub.2CH.sub.2OH                                                                         H     Cl   reddish                                                                  violet                                   __________________________________________________________________________    1272                                                                               ##STR541##   CH.sub.2CH.sub.2OH                                                                         CH.sub.3                                                                            H    bluish  red                         __________________________________________________________________________    1273                                                                               ##STR542##   CH.sub.2CH.sub.2OH                                                                         CH.sub.3                                                                            H    orange                              1274              CH.sub.2CH.sub.2OH                                                                         H     CH.sub.3                                                                           orange                              __________________________________________________________________________    1275                                                                               ##STR543##   CH.sub.2CH.sub.2OH                                                                         H     CH.sub.3                                                                           yellow                              1276              CH.sub.2CH.sub.2OH                                                                         C(CH.sub.3).sub.3                                                                   H    yellow                              1277              CH.sub.2CH.sub.2OH                                                                         H     OCH.sub.3                                                                          yellow                              1278              CH.sub.2CH.sub.2CH.sub.2OH                                                                 H     CH.sub.3                                                                           yellow                              __________________________________________________________________________    1279                                                                               ##STR544##   CH.sub.2CH.sub.2CH.sub.2OH                                                                 H     CH.sub.3                                                                           red                                 1280              CH.sub.2CH.sub.2OH                                                                         H     CH.sub.3                                                                           red                                 __________________________________________________________________________    1281                                                                               ##STR545##    CH.sub.2CH.sub.2OH                                                                        H     CH.sub.3                                                                           yellowish red                       __________________________________________________________________________    1282                                                                               ##STR546##   CH.sub.2CH.sub.2OH                                                                         H     CH.sub.3                                                                           orange                              __________________________________________________________________________

                                      TABLE 7                                     __________________________________________________________________________    Coupling component:                                                            ##STR547##                                                                   Example                                                                            Diazo component                                                                            R.sup.2            Shade                                    __________________________________________________________________________    1283                                                                                ##STR548##  H                  yellowish red                            1284              CH.sub.2CH.sub.2OH red                                      1285              CH.sub.2CH.sub.2CH.sub.2OH                                                                       red                                      1286                                                                                             ##STR549##        yellowish red                            1287              CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                         __________________________________________________________________________    1288                                                                                ##STR550##  H                  yellowish red                            1289              CH.sub.2CH.sub.2OH                                          1290              CH.sub.2CH.sub.2CH.sub.2OH                                  1291              CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                         __________________________________________________________________________    1292                                                                                ##STR551##  H                  orange                                   1293              CH.sub.2CH.sub.2OH                                          1294              CH.sub.2CH.sub.2CH.sub.2OH                                  1295              CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                         __________________________________________________________________________    1296                                                                                ##STR552##  H                                                           1297              CH.sub.2CH.sub.2OH                                          1298              CH.sub.2CH.sub.2CH.sub.2OH                                  __________________________________________________________________________    1299                                                                                ##STR553##  H                  red                                      1300              CH.sub.2CH.sub.2OH                                          1301              CH.sub.2CH.sub.2CH.sub.2OH                                  __________________________________________________________________________    1302                                                                                ##STR554##  H                  yellow                                   1303              CH.sub.2CH.sub.2OH                                          __________________________________________________________________________

                                      table 8                                     __________________________________________________________________________    dye:                                                                           ##STR555##                                                                   No.  Y      Y.sub.1                                                                            Y.sub.2                                                                            X      Shade                                            __________________________________________________________________________    1304 CN     H    H    H      yellow                                           1305 CN     NO.sub.2                                                                           H    CN     red                                              1306 CN     NO.sub.2                                                                           Cl   CN     red                                              1307 CN     Cl   H    H      orange                                           1308 H      NO.sub.2                                                                           H    CN     orange                                           1309 Cl     NO.sub.2                                                                           H    H      red                                              1310 Cl     Cl   CN   CN     orange                                           1311 CN     Br   H    CN     yellow                                           1312 CH.sub.3                                                                             NO.sub.2                                                                           H    CN     orange                                           1313 OCH.sub.3                                                                            NO.sub.2                                                                            H   CN     yellowish red                                    1314 SO.sub.2 CH.sub.3                                                                    NO.sub.2                                                                           H    CN     bluish red                                       1315 CF     H    H    CN     yellow                                           1316 CF.sub.3                                                                             Cl   H    CN     yellow                                           1317 CN     CN   H    CN     orange                                           1318 CN     NO.sub.2                                                                           Br   CN     red                                              1319 Cl     NO.sub.2                                                                           H    CN     yellowish red                                    1320 Br     NO.sub.2                                                                           H    CN     yellowish red                                    1321 H      NO.sub.2                                                                           H    H      red                                              1322 H      NO.sub.2                                                                           H    CONH.sub.2                                                                           yellowish red                                    __________________________________________________________________________

Particular value attaches for example to dyes of the formulae:

    __________________________________________________________________________    No.                                            Shade                          __________________________________________________________________________    1323                                                                               ##STR556##                                bluish red                     1324                                                                               ##STR557##                                bluish red                     1325                                                                               ##STR558##                                reddish violet                 1326                                                                               ##STR559##                                red                            1327                                                                               ##STR560##                                red                            1328                                                                               ##STR561##                                red                            1329                                                                               ##STR562##                                red                            1330                                                                               ##STR563##                                yellowish red                  1331                                                                               ##STR564##                                orange                         1332                                                                               ##STR565##                                yellowish red                  1333                                                                               ##STR566##                                yellowish                      __________________________________________________________________________                                                   red                        

                                      TABLE 9                                     __________________________________________________________________________    Dye                                                                                ##STR567##                                                               No. Y      Y.sup.1                                                                            Y.sup.2                                                                           E      R.sup.2    Shade                                   __________________________________________________________________________    1354                                                                              SO.sub.2 CH.sub.3                                                                    NO.sub.2                                                                           H   CH.sub.3                                                                             CH.sub.2CH.sub.2OH                                                                       red                                     1355                                                                              SO.sub.2 CH.sub.3                                                                    NO.sub.2                                                                           H   C.sub.3 H.sub.7 (n)                                                                  CH.sub.2CH.sub.2OH                                                                       red                                     1356                                                                              SO.sub.2 CH.sub.3                                                                    NO.sub.2                                                                           H   C.sub.5 H.sub.11 (n)                                                                 CH.sub.2CH.sub.2OH                                                                       red                                     1357                                                                              CN     NO.sub.2                                                                           H   CH.sub.3                                                                             CH.sub.2CH.sub.2OH                                                                       red                                     1358                                                                              CN     Cl   H   CH.sub.3                                                                             CH.sub.2CH.sub.2OH                                                                       yellow                                  1359                                                                              CN     H    H   CH.sub.3                                                                             CH.sub.2CH.sub.2OH                                                                       yellow                                  __________________________________________________________________________

                                      TABLE 10                                    __________________________________________________________________________    Dye                                                                               ##STR568##                                                                No.    Y      Y.sup.1                                                                              Y.sup.2                                                                              E      Shade                                      __________________________________________________________________________    1340   CN     H      H      CH.sub.3                                                                             yellow                                     1341   CN     NO.sub.2                                                                             H      CH.sub.3                                                                             red                                        1342   CN     NO.sub.2                                                                             Cl     CH.sub.3                                                                             red                                        1343   CN     Cl     H      CH.sub.3                                                                             yellow                                     1344   H      NO.sub.2                                                                             H      CH.sub.3                                                                             orange                                     __________________________________________________________________________

EXAMPLE 1356

9.8 parts of 2-amino-5,nitrobenzonitrile is added to 0° to 4° C inportions while stirring well to a mixture of 48 parts of concentratedsulfuric acid and 19.6 parts of 23% nitrosylsulfuric acid. The diazosolution is stirred for from four to five hours at 0° to 4° C and thediazonium salt mixture is then added in portions to a solution orsuspension, cooled to 0° C, of 23.5 parts of the coupling component ofthe formula: ##STR569## which contains a minor fraction of the couplingcomponent of the formula: ##STR570## in a mixture of 150 parts by volumeof glacial acetic acid, 20 parts by volume of concentrated hydrochloricacid, 1 part of sulfamic acid and 500 parts by volume of water. Sodiumacetate and ice are added during coupling so that the pH of the mixtureis always from 0 to 2, the temperature is about 0° C and the mixtureremains easily stirred. After coupling is over (it proceeds very rapidlyat pH 1 to 2) the pricipitated dye mixture of the formula: ##STR571##(which contains a minor amount of the 2,6-dialkylaminopyridine isomer)is suction filtered and the residue washed with water and dried. Areddish brown powder is obtained which dissolves in dimethylformamidewith a red color and dyes polyethylene terephthalate cloth red shades ofexcellent light fastness.

EXAMPLE 1357

8.8 parts of the diazo component of the formula: ##STR572## is stirredin 24 parts of concentrated sulfuric acid at 10° to 15° C. The whole isthen cooled to 8° to 10° C and at this temperature 70 parts by volume ofglacial acetic acid and 12 parts by volume of propionic acid are addedwhile cooling. After further cooling to 0° to 4° C 13 parts ofnitrosylsulfuric acid is dripped in and the whole is stirred for threehours at 0° to 4° C. The diazonium salt solution thus obtained is addedto 13.1 parts of a solution or suspension, cooled to 0° C, of thecoupling component of the formula: ##STR573## (a minor portion of thecoupling component consisting of the 2,6-dialkylaminopyridine isomer) ina mixture of 150 parts by volume of glacial acetic acid, 15 parts byvolume of concentrated hydrochloric acid, 500 parts of water and 1 partof sulfamic acid.

Ice and sodium acetate are added during coupling so that the temperaturedoes not rise above 0° C and the pH remains at from 2 to about 0.Ice-water may also be added if the mixture becomes too difficult tostir.

Coupling is rapidly ended at pH 2. The precipitated dye mixture of theformulae: ##STR574## is filtered off, washed with water and dried. Abrown powder is obtained which dissolves in dimethylformamide with anorange red color and dyes polyethylene terephthalate cloth orange shadesof excellent light fastness.

EXAMPLE 1358

5.5 parts of p-nitroaniline is stirred with 40 parts by volume of waterand 15 parts by volume of concentrated hydrochlirc acid. The whole isthen diluted with ice and hydrochloric acid to a volume of 200 parts byvolume, 13 parts by volume of 23% sodium nitrite solution is added andthe whole is stirred for two hours. After the diazonium salt solutionhas been filtered any excess of nitrous acid present is destroyed asusual and the diazonium salt solution is added to a solution ordispersion, cooled to 5° C, of 10 parts of the coupling component:##STR575## in 250 parts of water and 20 parts of concentratedhydrochloric acid. The pH of the coupling mixture is raised to 2 to 3 bystewing in sodium acetate so that the coupling is rapidly ended. Theprecipitated dye of the formula: ##STR576## is suction filtered, washedwith water and dried. About 15 parts of a yellowish red powder isobtained which dissolves in dimethylformamide with an orange color anddye polyethylene terephthalate cloth full orange shades having very goodfastness to light and dry-heat pleating the setting by the carrier andHT methods.

The dyes set out in the following Tables can be prepared by the methodsdescribed in Examples 1356 to 1358:

                                      TABLE 1                                     __________________________________________________________________________     ##STR577##                                                                   Example                                                                            D-NH          Z.sup.1              Z.sub.2        Shade                  __________________________________________________________________________    1359                                                                                ##STR578##   (CH.sub.2).sub.3O(CH.sub.2CH.sub.2O).sub.2CH.sub.2                                                 (CH.sub.2).sub.3 O(CH.sub.2).sub.4                                             OH            yellow                 1360                                                                                              ##STR579##          (CH.sub.2).sub.3 O(CH.sub.2).sub.6                                            H              "                      1361               "                    (CH.sub.2).sub.3 O(CH.sub.2                                                   CH.sub.2 O).sub.2 C.sub.2                                                                    ".sub.5                __________________________________________________________________________    1362                                                                                ##STR580##   H                    (CH.sub.2).sub.3 O(CH.sub.2).sub.6                                            H              yellowish              __________________________________________________________________________                                                           red                    1363                                                                                ##STR581##   H                    (CH.sub.2).sub.3 O(CH.sub.2).sub.6                                             OH            red                    1364                                                                                ##STR582##                                                                                  ##STR583##          CH.sub.2CH.sub.2OH                                                                           orange                 1365 "                                                                                            ##STR584##          "              orange                 1366                                                                                ##STR585##                                                                                  ##STR586##          "              yellow                 1367                                                                                ##STR587##   "                    "              red                    __________________________________________________________________________

                                      TABLE 2                                     __________________________________________________________________________     ##STR588##                                                                   Ex.                                                                              D-NH.sub.2         Z.sup.1            Z.sup.2         Shade                __________________________________________________________________________    1368                                                                              ##STR589##   (CH.sub.2).sub.3OC.sub.2 H.sub.4OC.sub.2 H.sub.5                                                      "               yellow               1369                                                                             "             (CH.sub.2).sub.3OC.sub.2 H.sub.4OC.sub.6 H.sub.5                                                      "                "                   1370                                                                             "                                                                                            ##STR590##             "                "                   1371                                                                             "                                                                                            ##STR591##             CH.sub.2CH.sub.2OH                                                                             "                   1372                                                                             "             (CH.sub.2).sub.3OCH.sub.2CH.sub.2C.sub.6 H.sub.5                                                      "                "                   1373                                                                             "             (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5                                                              "                "                   1374                                                                             "             H                       (CH.sub.2).sub.3OCH.sub.2C.sub.6                                              H.sub.5          "                   1375                                                                             "             H                       (CH.sub.2).sub.3O(C.sub.2                                                     H.sub.4).sub.3 C.sub.6 H.sub.5                                                                 "                   1376                                                                              ##STR592##   (CH.sub.2).sub.3OCH.sub.2CH.sub.2 OCH.sub.2 C.sub.6                           H.sub.5                 CH.sub.2CH.sub.2OH                                                                            "                    1377                                                                             "             H                       (CH.sub.2).sub.3O(C.sub.2                                                     H.sub.4 O).sub.3 C.sub.6                                                                       "sub.5              1378                                                                             "                                                                                            ##STR593##             CH.sub.2CH.sub.2OH                                                                             "                   1379                                                                             "             (CH.sub.2).sub.2OC.sub.6 H.sub.5                                                                      "                "                   1380                                                                             "             (CH.sub.2).sub.3OC.sub.6 H.sub.5                                                                       "               "                   1381                                                                             "                                                                                            ##STR594##             "                "                   1382                                                                             "             (CH.sub.2).sub.3O(CH.sub.2).sub.6OH                                                                   "                "                   1383                                                                             "                                                                                            ##STR595##             "                "                   1384                                                                              ##STR596##                                                                                  ##STR597##             "               orange               1385                                                                             "             (CH.sub.2).sub.3(OC.sub.2 H.sub.4).sub.2OCH.sub.3                                                     "                "                   1386                                                                             "             (CH.sub.2).sub.3(OC.sub.2 H.sub.4).sub.3OC.sub.2                                                      ".sub.5          "                   1387                                                                             "             (CH.sub.2).sub.3(OC.sub.2 H.sub.4).sub.4OC.sub.2                                                      ".sub.5          "                   1388                                                                             "             (CH.sub.2).sub.3(OCHCH.sub.2).sub.2OCH.sub.3                                                          "                "                   1389                                                                             "              H                      (CH.sub.2).sub.3(OC.sub.2                                                     H.sub.4).sub.3 OCH.sub.3                                                                       "                   1390                                                                             "             H                                                                                                      ##STR598##      "                   1391                                                                             "             H                       CH.sub.2CHOC.sub.6 H.sub.5                                                                     "                   1392                                                                             "             H                       (CH.sub.2).sub.3(O CH.sub.2CH.sub                                             .2).sub.2 - OC.sub.6 H.sub.5                                                                  "                    1393                                                                             "             H                                                                                                      ##STR599##                          1394                                                                             "             (CH.sub.2).sub.3(OC.sub.2 H.sub.4).sub.2OC.sub.6                                                      CH.sub.2CH.sub.2OH                                                                             "                   1395                                                                             "                                                                                            ##STR600##             "                "                   1396                                                                             "             (CH.sub.2).sub.3OC.sub.2 H.sub.4OCH.sub.2C.sub.6                                                      ".sub.5          "                   1397                                                                              ##STR601##   (CH.sub.2).sub.3OC.sub.2 H.sub.4OCH.sub.2C.sub.6                                                      ".sub.5          "                   1398                                                                             "             (CH.sub.2).sub.3OC.sub.2 H.sub.4OCH(CH.sub.3).sub.2                                                   "                "                   1399                                                                             "             (CH.sub.2).sub.3OC.sub.2 H.sub.4C.sub.6 H.sub.5                                                       "                "                   1400                                                                              ##STR602##   "                       "               yellowish red        1401                                                                             "             "                       (CH.sub.2).sub.3OH                                                                             "                   1402                                                                             "             (CH.sub.2).sub.3(OC.sub.2 H.sub.4).sub.2OC.sub.6                                                      ".sub.5          "                   1403                                                                             "                                                                                            ##STR603##             CH.sub.2CH.sub.2OH                                                                             "                   1404                                                                              ##STR604##   H                       (CH.sub.2).sub.3OCH.sub.2C.sub.                                               6 H.sub.5        "                   1405                                                                             "             H                       (CH.sub.2).sub.3OC.sub.2 H.sub.4                                              OC.sub.6 H.sub.5                                                                               "                   1406                                                                             "             (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5                                                              CH.sub.2CH.sub.2OH                                                                             "                   1407                                                                              ##STR605##   "                       "                "                   1408                                                                             "             (CH.sub.2).sub.3OCHCH.sub.2OC.sub.6 H.sub.5                                                           "                "                   1409                                                                              ##STR606##   H                       (CH.sub.2).sub.3(OCH.sub.2                                                    CH.sub.2).sub.3 OC.sub.6                                                                      yellow5              1410                                                                             "                                                                                            ##STR607##             CH.sub.2CH.sub.2OH                                                                             "                   1411                                                                             "             (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5                                                              "                 "                  1412                                                                              ##STR608##   (CH.sub.2).sub.3(OC.sub.2 H.sub.4).sub.3OC.sub.6                                                      CH.sub.2CH.sub.2OH                                                                             "                   1413                                                                             "             (CH.sub.2).sub.3(OC.sub.2 H.sub.4).sub.4OC.sub.2                                                      ".sub.5          "                   1414                                                                             "             "                       (CH.sub.2).sub.3OH                                                                             "                   1415                                                                              ##STR609##   "                       "                "                   1416                                                                             "             H                       (CH.sub.2).sub.3OCH.sub.2C.sub.6                                              H.sub.5          "                   1417                                                                              ##STR610##                           "                "                   1418                                                                             "             (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5                                                              CH.sub.2CH.sub.2OH                                                                             "                   1419                                                                              ##STR611##   "                       "               orange               1420                                                                              ##STR612##                                                                                  ##STR613##             CH.sub.2CH.sub.2OH                                                                             "                   1421                                                                              ##STR614##   "                       "                red                 1422                                                                             "             (CH.sub.2).sub.3O(CH.sub.2).sub.6OH                                                                   H               yellowish red        1423                                                                             "             H                       (CH.sub.2).sub.3O(CH.sub.2).sub.6                                              OH              "                   1424                                                                             "             CH.sub.2COC.sub.6 H.sub.5                                                                             CH.sub.2CH.sub.2OH                                                                            red                  1425                                                                             "             CH.sub.2CH.sub.2OC.sub.6 H.sub.5                                                                      "                "                   1426                                                                              ##STR615##   H                       (CH.sub.2).sub.3O(CH.sub.2).sub.6                                             H               orange               1427                                                                             "             H                       (CH.sub.2).sub.3O(C.sub.2                                                     H.sub.4 O).sub.2C.sub.6 H.sub.5                                                                "                   1428                                                                             "             H                       (CH.sub.2).sub.3OCH.sub.2C.sub.6                                              H.sub.5          "                   1429                                                                             "             (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5                                                              H                "                   1430                                                                             "             (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5                                                              "                "                   1431                                                                             "             (CH.sub.2).sub.3OC.sub.2 H.sub.4OC.sub.2 H.sub.5                                                      "                "                   1432                                                                             "                                                                                            ##STR616##             "                "                   1433                                                                             "             (CH.sub.2).sub.3(OCHCH.sub.2).sub.2OCH.sub.3                                                          "                "                   1434                                                                              ##STR617##   (CH.sub.2).sub.3O (CH.sub.2 CH.sub.2 O).sub.2 CH.sub.3                                                "               yellowish red        1435                                                                             "             (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5                                                              "                "                   1436                                                                              ##STR618##   "                       "               red                  1437                                                                             "             H                       (CH.sub.2).sub.3OCH.sub.2C.sub.6                                              H.sub.5          "                   1438                                                                             "             (CH.sub.2).sub.3OC.sub.2 H.sub.4 OC.sub.4 H.sub.9                                                     CH.sub.2CH.sub.2OH                                                                             "                   1439                                                                             "             (CH.sub.2).sub.3OC.sub.2 H.sub.4OCH(CH.sub.3).sub.2                                                   "                "                   1440                                                                             "             (CH.sub.2).sub.3O(CH.sub.2).sub.2C.sub.6 H.sub.5                                                      CH.sub.2CH.sub.2OH                                                                             "                   1441                                                                             "             (CH.sub.2).sub.3O(C.sub.2 H.sub.4 O).sub.2C.sub.6                             H.sub.5                 "                "                   1442                                                                              ##STR619##   "                       "                "                   1443                                                                             "             (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5                                                              "                "                   1444                                                                             "             "                       (CH.sub.2).sub.3OH                                                                             "                   1445                                                                             "             (CH.sub.2).sub.3O(C.sub.2 H.sub.4 O).sub.2 C.sub.6                            H.sub.5                 CH.sub.2CH.sub.2OH                                                                             "                   1446                                                                             "             H                       (CH.sub.2).sub.3OCH.sub.2C.sub.6                                              H.sub.5          "                   1447                                                                              ##STR620##   (CH.sub.2).sub.3O(CH.sub.2).sub.2OH                                                                   H               orange               1448                                                                             "             (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5                                                              "               reddish blue         1449                                                                             "             "                       CH.sub.2CH.sub.2OH                                                                             "                   1450                                                                              ##STR621##   "                       "               violet               __________________________________________________________________________

                                      TABLE 3                                     __________________________________________________________________________     ##STR622##                                                                   Ex.                                                                              DNH.sub.2   Z.sup.1       Z.sup.2   Shade                                  __________________________________________________________________________    1451                                                                              ##STR623## (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5                                                    CH.sub.2CH.sub.2OH                                                                      reddish                                1452                                                                              ##STR624## (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5                                                    CH.sub.2CH.sub.2OH                                                                      bluish red                             1453                                                                              ##STR625## (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5                                                    CH.sub.2CH.sub.2OH                                                                      red                                    __________________________________________________________________________

                  TABLE 4                                                         ______________________________________                                        Coupling component:                                                            ##STR626##                                                                   ______________________________________                                    

in coupling with these coupling components mixtures are formed becausethe coupling may take place in the 3-position and also in the 5-positionof the pyridine ring:

    __________________________________________________________________________       Diazo                                                                      No.                                                                              component       Z.sup.1        Z.sup.2   Shade                             __________________________________________________________________________    1454                                                                              ##STR627##     (CH.sub.2).sub.3OCH.sub.2 C.sub.6 H.sub.5                                                    CH.sub.2CH.sub.2OH                                                                      greenish blue                     1455                                                                             "               "              (CH.sub.2).sub.3OH                                                                      "                                 1456                                                                             "               (CH.sub.2).sub.3OC.sub.2 H.sub.4OC.sub.2 H.sub.5                                             CH.sub.2CH.sub.2OH                                                                      "                                 1457                                                                              ##STR628##     (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5                                                     "         reddish violet                    1458                                                                              ##STR629##     "              "         "                                 1459                                                                             "                                                                                              ##STR630##    "         "                                 1460                                                                              ##STR631##     "              "         "                                 1461                                                                             "               (CH.sub.2).sub.4OCH.sub.2C.sub.6 H.sub.5                                                     "         "                                 1462                                                                              ##STR632##     CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5                                                      (CH.sub.2).sub.3OH                                                                      bluish red                        __________________________________________________________________________

The dyes set out in Table 5 are also particularly valuable. They aredistinguished by high yield and high fastness to dry-heat pleating andsetting.

                  TABLE 5                                                         ______________________________________                                        Coupling component:                                                            ##STR633##                                                                         Diazo                                                                   No.   component                  Shade                                        ______________________________________                                        1463                                                                                 ##STR634##         2      red                                          1464  "                   3      "                                            1465                                                                                 ##STR635##         2      bluish red                                   1466  "                   3      "                                            1467                                                                                 ##STR636##         2      yellowish red                                1468  "                   3      "                                            1469                                                                                 ##STR637##         2      bluish red                                   1470  "                   3      "                                            1471                                                                                 ##STR638##         2      "                                            1472  "                   3      "                                            1473                                                                                 ##STR639##         2      "                                            1484  "                   3      "                                            1475                                                                                 ##STR640##         2      yellow                                       1476  "                   3      "                                            1477                                                                                 ##STR641##         2      reddish violet                               1478  "                   3      "                                            1479                                                                                 ##STR642##         2      orange                                       1480  "                   3      "                                            1481                                                                                 ##STR643##         2      red                                          1482  "                   3      "                                            1483                                                                                 ##STR644##         2      orange                                       1484  "                   3      "                                            ______________________________________                                    

                                      TABLE 6                                     __________________________________________________________________________    Coupling component:                                                                               ##STR645##                                                No. D-NH.sub.2  n  Z.sup.1       Shade                                        __________________________________________________________________________    1485                                                                               ##STR646## 2  (CH.sub.2).sub.3O(CH.sub.2).sub.2 OH                                                        yellow                                       1486                                                                              "           3  "             "                                            1487                                                                              "           6  "             "                                            1488                                                                               ##STR647## 2  "             orange                                       1489                                                                              "           6  "             "                                            1490                                                                               ##STR648## 2  "             yellowish red                                1491                                                                              "           3  "             "                                            1492                                                                               ##STR649## 2  "             bluish red                                   1493                                                                              "           3  "             "                                            1494                                                                               ##STR650## 2  (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5                                                    yellow                                       1495                                                                               ##STR651## 2  "             "                                            __________________________________________________________________________        The dye of the formula:                                                   1496                                                                               ##STR652##                  red                                          __________________________________________________________________________

                                      TABLE 7                                     __________________________________________________________________________    Coupling component:                                                                        ##STR653##                                                       No.                                                                              Diazo component Z.sup.2           Shade                                    __________________________________________________________________________    1497                                                                              ##STR654##     C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                             yellow                                   1498                                                                             "               C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3                                                      "                                        1499                                                                              ##STR655##                                                                                    ##STR656##       "                                        1500                                                                             "               C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                             "                                        1501                                                                              ##STR657##     "                 "                                        1502                                                                             "                                                                                              ##STR658##       "                                        1503                                                                              ##STR659##     C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                             "                                        1504                                                                              ##STR660##     "                 orange                                   1505                                                                              ##STR661##     "                 "                                        1506                                                                              ##STR662##     "                 orange                                   1507                                                                             "               (CH.sub.2).sub.3 O(CH.sub.2).sub.6 OH                                                           "                                        1508                                                                              ##STR663##     C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                             yellowish red                            1509                                                                             "               (CH.sub.2).sub.3 (OC.sub.2 H.sub.4).sub.2 OCH.sub.3                                             "                                        1510                                                                              ##STR664##     C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                             "                                        1511                                                                              ##STR665##     "                 "                                        1512                                                                              ##STR666##     "                 yellow                                   1513                                                                              ##STR667##     "                 orange                                   1514                                                                              ##STR668##     "                 yellow                                   1515                                                                              ##STR669##     "                 "                                        1516                                                                              ##STR670##     "                 "                                        1517                                                                              ##STR671##     "                 orange                                   1518                                                                              ##STR672##     "                 yellow                                   1519                                                                              ##STR673##     "                 "                                        1520                                                                              ##STR674##     "                 "                                        1521                                                                              ##STR675##     "                 yellowish red                            1522                                                                              ##STR676##     "                 "                                        1523                                                                              ##STR677##     "                 red                                      1524                                                                              ##STR678##     "                 "                                        1525                                                                              ##STR679##     "                 "                                        1526                                                                              ##STR680##     "                 "                                        1527                                                                              ##STR681##     "                 "                                        1528                                                                              ##STR682##     "                 yellowish red                            1529                                                                              ##STR683##     "                 "                                        1530                                                                              ##STR684##     "                 bluish red                               1531                                                                              ##STR685##     "                 red                                      1532                                                                              ##STR686##     "                 yellow                                   1533                                                                              ##STR687##     "                 "                                        1534                                                                              ##STR688##     (CH.sub.2).sub.3 O(CH.sub.2).sub.4 OH                                                           red                                      1535                                                                              ##STR689##     "                 reddish blue                             1536                                                                             "               C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                             "                                        1537                                                                              ##STR690##     "                 "                                        1538                                                                              ##STR691##     "                 "                                        1539                                                                              ##STR692##     "                 yellowish blue                           1540                                                                              ##STR693##     "                 yellow                                   1541                                                                              ##STR694##     "                 "                                        1542                                                                              ##STR695##     "                 bluish red                               1543                                                                              ##STR696##     "                 "                                        1544                                                                              ##STR697##     "                 "                                        1545                                                                             "               (CH.sub.2).sub.3 O(CH.sub.2).sub.4 OH                                                           "                                        1546                                                                              ##STR698##     C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                             violet                                   1547                                                                              ##STR699##     C.sub.2 H.sub. 4 OC.sub.2 H.sub.4 OH                                                            violet                                   1548                                                                             "X = CN         "                 bluish violet                            1549                                                                              ##STR700##     "                 orange                                   1550                                                                              ##STR701##     "                 "                                        1551                                                                              ##STR702##     "                 violet                                   1552                                                                              ##STR703##     "                 bluish red                               1553                                                                              ##STR704##     "                 "                                        1554                                                                              ##STR705##                                                                                    ##STR706##       orange                                   1555                                                                             "               (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OH                                                           "                                        1556                                                                             "                                                                                              ##STR707##       "                                        1557                                                                             "                                                                                              ##STR708##       "                                        1558                                                                             "                                                                                              ##STR709##       "                                        1559                                                                             "               (CH.sub.2).sub.3 OC.sub.6 H.sub.5                                                               "                                        1560                                                                             "               (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5                                                      "                                        1561                                                                             "               (CH.sub.2).sub.3 OC.sub.2 H.sub.4 C.sub.6 H.sub.5                                               "                                        1562                                                                             "               (CH.sub.2).sub.3 OC.sub.2 H.sub.4 OC.sub.6 H.sub.5                                              "                                        1563                                                                             "               CH.sub.2 CHOHC.sub.6 H.sub.5                                                                    "                                        __________________________________________________________________________

when 2-cyano-4-chloroaniline is used in the case of Examples 1554 to1563, compounds which give yellow shades are obtained.

                  TABLE 8                                                         ______________________________________                                        Coupling component:                                                            ##STR710##                                                                   No.  Diazo component   Z.sup.1      Shade                                     ______________________________________                                        1564                                                                                ##STR711##       (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OH                                                      yellow                                    1565                                                                                ##STR712##                                                                                      ##STR713##  "                                         1566                                                                                ##STR714##       C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                        "                                         1567                                                                                ##STR715##       "            orange                                    1568                                                                                ##STR716##       "            "                                         1569                                                                                ##STR717##       "            yellow                                    1570                                                                                ##STR718##       "            yellow- ish red                           1571                                                                                ##STR719##       "            "                                         1572                                                                                ##STR720##       "            red                                       1573                                                                                ##STR721##       "            "                                         1574                                                                                ##STR722##       (CH.sub.2).sub.3 O(CH.sub.2).sub.4 OH                                                      red                                       1575                                                                                ##STR723##       C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                        "                                         1576                                                                                ##STR724##       "            violet                                    1577                                                                                ##STR725##       "            reddish  blue                             1578                                                                                ##STR726##       "            blue                                      1579                                                                                ##STR727##       "            red                                       1580                                                                                ##STR728##       "            bluish red                                1581                                                                                ##STR729##       "            bluish red                                1582                                                                                ##STR730##       "            red                                       ______________________________________                                    

                  TABLE 9                                                         ______________________________________                                        Coupling component:                                                            ##STR731##                                                                   No.  Diazo component                                                                             X        Z.sup.2   Shade                                   ______________________________________                                        1583                                                                                ##STR732##   H        C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                     yellow- ish red                         1584                                                                                ##STR733##   H        "         "                                       1585                                                                                ##STR734##   H        "         orange                                  1586                                                                                ##STR735##   CONH.sub.2                                                                             "         red                                     1587                                                                                ##STR736##   "        "         reddish violet                          ______________________________________                                    

EXAMPLE 1588

A mixture of 187 parts of 2,6-dichloro-3-cyano-4-ethylpyridine, 500parts of methanol and 135 parts of 2-phenylpropylamine-(1) is stirredfor an hour at from about 25° to a maximum of 55° C, then 105 parts oftriethylamine is added within fifteen minutes and the whole is stirredfor another six hours at about 45° to 55° C. About 250 parts by volumeof methanol is distilled off at subatmospheric pressure with the excesstriethylamine, the whole is allowed to cool somewhat and the residue isadded while stirring to a mixture of about 1500 parts of water, 500parts of ice and 50 parts of concentrated hydrochloric acid. Stirring iscontinued for one hour and the precipitate is suction filtered anddried. About 265 parts of a colorless powder is obtained which melts at85° to 90° C.

27.5 parts of this powder is stirred with about 60 parts ofβ-hydroxyethylamine for from four to five hours at 130° to 155° C. Thewhole is allowed to cool and 200 parts by volume of glacial acetic acidand 30 parts by volume of concentrated hydrochloric acid are added tothe mixture. A solution of the coupling component of the probableformula: ##STR737## is obtained which contains a minor proportion of thecoupling component of the probable formula: ##STR738##

The coupling component mixture has about 50 parts of ice added to it andis cooled to about 0° C. Then there are added in portions at the sametime about 100 parts of ice and a solution of diazotized2-amino-4-nitro-benzonitrile which has been prepared as follows: 16.3parts of 2-amino-5-nitrobenzonitrile is added while stirring at 0° to 4°C into a mixture of 50 parts of concentrated sulfuric acid and 13 partsof 23% nitrosylsulfuric acid so that the temperature does not at anytime rise above 4° C. The whole is stirred for four hours at 0° to 5° Cand then coupled as described above. In order to achieve rapidcompletion of the coupling, which should proceed at about 0° C, the pHof the mixture is adjusted to be from 1.5 to 2.5 by adding sodiumacetate. If the mixture should become difficult to stir during thecoupling, ice-water may be added.

The mixture is stirred for another hour, heated with steam to 60° to 80°C, suction filtered, washed with water and dried. About 47 parts of areddish brown powder of the probable formula: ##STR739## is obtainedwhich contains a smaller dye fraction of the 2,6-alkyl-aminopyridineisomers. It dissolves in dimethylformamide with a red color and dyespolyethylene terephthalate cloth full red shades having excellentfastness properties.

                  TABLE 1                                                         ______________________________________                                         ##STR740##                                                                   ______________________________________                                        No.    R        X             Y      Shade                                    ______________________________________                                        1589   C.sub.2 H.sub.5                                                                        CH.sub.2CH.sub.2OH                                                                          C.sub.6 H.sub.5                                                                      bluish red                               ______________________________________                                    

                                      TABLE 2                                     __________________________________________________________________________     ##STR741##                                                                   __________________________________________________________________________    No.                                                                              R    X         Y             Shade                                         __________________________________________________________________________    1590                                                                             C.sub.3 H.sub.7                                                                    CH.sub.2CH.sub.2OH                                                                      (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5                                                    red                                           1591                                                                             C.sub.3 H.sub.7                                                                    H         C.sub.6 H.sub.5                                                                             bluish red                                    __________________________________________________________________________

                                      TABLE 3                                     __________________________________________________________________________     ##STR742##                                                                   __________________________________________________________________________    No.                                                                              R    X         Y             Shade                                         __________________________________________________________________________    1592                                                                             C.sub.3 H.sub.7                                                                    CH.sub.2CH.sub.2OH                                                                      (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5                                                    red                                           1593                                                                             C.sub.3 H.sub.7                                                                    H         C.sub.6 H.sub.5                                                                             bluish red                                    __________________________________________________________________________

                                      TABLE 4                                     __________________________________________________________________________     ##STR743##                                                                   __________________________________________________________________________    No.                                                                              R    X         Y          Shade                                            __________________________________________________________________________    1594                                                                             C.sub.3 H.sub.7                                                                    CH.sub.2CH.sub.2OH                                                                      C.sub.6 H.sub.5                                                                          bluish red                                       1595                                                                             C.sub.3 H.sub.7                                                                    CH.sub.2CH.sub.2OH                                                                       ##STR744##                                                                              red                                              __________________________________________________________________________

                                      TABLE 5                                     __________________________________________________________________________     ##STR745##                                                                   __________________________________________________________________________    No.                                                                              R    X                Y    Shade                                           __________________________________________________________________________    1596                                                                             C.sub.2 H.sub.5                                                                    CH.sub.2CH.sub.2OCH.sub.2 CH.sub.2OH                                                           C.sub.6 H.sub.5                                                                    yellowish red                                   1597                                                                             C.sub.2 H.sub.5                                                                    CH.sub.2CH.sub.2OH                                                                             C.sub.6 H.sub.5                                                                    yellowish red                                   __________________________________________________________________________

                                      TABLE 6                                     __________________________________________________________________________     ##STR746##                                                                   __________________________________________________________________________    No.                                                                              R    X                  Y    Shade                                         __________________________________________________________________________     1598                                                                            C.sub.2 H.sub.5                                                                    CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              C.sub.6 H.sub.5                                                                    yellowish red                                 1599                                                                             C.sub.2 H.sub.5                                                                    CH.sub.2CH.sub.2OH C.sub.6 H.sub.5                                                                    yellowish red                                 __________________________________________________________________________

                                      TABLE 7                                     __________________________________________________________________________     ##STR747##                                                                   __________________________________________________________________________    No.                                                                              R     X                  Y             Shade                               __________________________________________________________________________    1600                                                                             C.sub.3 H.sub.7 (n)                                                                 CH.sub.2CH.sub.2OH                                                                                ##STR748##   reddish orange                      1601                                                                             C.sub.3 H.sub.7 (n)                                                                 CH.sub.2CH.sub.2OH C.sub.6 H.sub.5                                                                             yellowish red                       1602                                                                             C.sub.2 H.sub.5                                                                     CH.sub.2CH.sub.2OH C.sub.6 H.sub.5                                                                             yellowish red                       1603                                                                             C.sub.2 H.sub.5                                                                     CH.sub.2CH.sub.2OCH.sub.2OH.sub.2OH                                                              C.sub.6 H.sub.5                                                                             yellowish red                       __________________________________________________________________________

                                      TABLE 8                                     __________________________________________________________________________     ##STR749##                                                                   No. R     X          Y               Shade                                    __________________________________________________________________________    1604                                                                              C.sub.2 H.sub.5                                                                     CH.sub.2CH.sub.2OH                                                                       (CH.sub.2).sub.3O(CH.sub.2).sub.6OH                                                           red                                      1605                                                                              C.sub.3 H.sub.7 (n)                                                                 CH.sub.2CH.sub.2OH                                                                        ##STR750##     "                                        1606                                                                              C.sub.2 H.sub.5                                                                     CH.sub.2CH.sub.2OH                                                                        ##STR751##     "                                        1607                                                                              C.sub.3 H.sub.7 (n)                                                                 CH.sub.2CH.sub.2OH                                                                       C.sub.6 H.sub.5 "                                        1608                                                                              C.sub.2 H.sub.5                                                                     CH.sub.2CH.sub.2OH                                                                       C.sub.6 H.sub.5 "                                        1609                                                                              C.sub.3 H.sub.7 (n)                                                                 CH.sub.2CH.sub.2OH                                                                        ##STR752##     "                                        1610                                                                              C.sub. 3 H.sub.7 (n)                                                                CH.sub.2CH.sub.2OH                                                                        ##STR753##     "                                        __________________________________________________________________________

                                      table 9                                     __________________________________________________________________________     ##STR754##                                                                   No. R     X             Y          Shade                                      __________________________________________________________________________    1611                                                                              C.sub.2 H.sub.5                                                                     CH.sub.2CH.sub.2CH.sub.2OH                                                                  C.sub.6 H.sub.5                                                                          yellow to                                                                     orange                                     1612                                                                              C.sub.2 H.sub.5                                                                     CH.sub.2CH.sub.2OH                                                                          C.sub.6 H.sub.5                                                                          "                                          1613                                                                              C.sub.3 H.sub.7 (n)                                                                 H                                                                                            ##STR755##                                                                              yellow                                     1614                                                                              C.sub.3 H.sub.7 (n)                                                                  ##STR756##   H          "                                          1615                                                                              C.sub.3 H.sub.7 (n)                                                                  ##STR757##   CH.sub.2CH.sub.2OH                                                                       "                                          __________________________________________________________________________

                  table 10                                                        ______________________________________                                         ##STR758##                                                                   no.  R         X                Y      Shade                                  ______________________________________                                        1616 C.sub.3 H.sub.7 (n)                                                                     CH.sub.2CH.sub.2OH                                                                             C.sub.6 H.sub.5                                                                      yellow                                 1617 C.sub.3 H.sub.7 (n)                                                                     CH.sub.2CH.sub.2CH.sub.2OH                                                                     C.sub.6 H.sub.5                                                                      "                                      ______________________________________                                    

                                      table 11                                    __________________________________________________________________________     ##STR759##                                                                   no.                                                                              R     X         Y              Shade                                       __________________________________________________________________________    1618                                                                             C.sub.2 H.sub.5                                                                     H         (CH.sub.2).sub.3O(CH.sub.2).sub.6OH                                                          yellowish red                               1619                                                                             C.sub.3 H.sub.7 (n)                                                                 CH.sub.2CH.sub.2OH                                                                       ##STR760##    red                                         1620                                                                             C.sub.2 H.sub.5                                                                     CH.sub.2CH.sub.2OH                                                                       ##STR761##    "                                           1621                                                                             C.sub.3 H.sub.7 (n)                                                                 CH.sub.2CH.sub.2OH                                                                      C.sub.6 H.sub.5                                                                              "                                           1622                                                                             C.sub.2 H.sub.5                                                                     CH.sub.2CH.sub.2OH                                                                      C.sub.6 H.sub.5                                                                              "                                           1623                                                                             C.sub.3 H.sub.7 (n)                                                                 CH.sub.2CH.sub.2 OH                                                                      ##STR762##    "                                           1624                                                                             C.sub.3 H.sub.7 (n)                                                                 CH.sub.2CH.sub.2OH                                                                       ##STR763##    "                                           __________________________________________________________________________

                  tale 12                                                         ______________________________________                                         ##STR764##                                                                   no.   R         X              Y      Shade                                   ______________________________________                                        1625  C.sub.2 H.sub.5                                                                         CH.sub.2CH.sub.2OH                                                                           C.sub.6 H.sub.5                                                                      red                                     ______________________________________                                    

                  TABLE 13                                                        ______________________________________                                         ##STR765##                                                                   No.   R         X              Y      Shade                                   ______________________________________                                        1626  C.sub.2 H.sub.5                                                                         CH.sub.2CH.sub.2OH                                                                           C.sub.6 H.sub.5                                                                      red                                     ______________________________________                                    

                                      TABLE 14                                    __________________________________________________________________________     ##STR766##                                                                   No. R      X                   Y     Shade                                    __________________________________________________________________________    1627                                                                              C.sub.2 H.sub.5                                                                      CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                               C.sub.6 H.sub.5                                                                     blue                                     1628                                                                              C.sub.2 H.sub.5                                                                      CH.sub.2CH.sub.2CH.sub.2OH                                                                        C.sub.6 H.sub.5                                                                     blue                                     1629                                                                              C.sub.2 H.sub.5                                                                      CH.sub.2CH.sub.2OH  C.sub.6 H.sub.5                                                                     blue                                     1630                                                                              C.sub.3 H.sub.7 (n)                                                                  (CH.sub.2).sub.3O(CH.sub.2).sub.6OH                                                               H     violet                                   __________________________________________________________________________

                                      TABLE 15                                    __________________________________________________________________________     ##STR767##                                                                   No. R     X              Y                     Shade                          __________________________________________________________________________    1631                                                                              C.sub.3 H.sub.7 (n)                                                                 CH.sub.2CH.sub.2OH                                                                           (CH.sub.2).sub.3O(CH.sub.2).sub.2O(CH.sub.2).sub.                             2OCH.sub.3            reddish violet                 1632                                                                              C.sub.3 H.sub.7 (n)                                                                 H              C.sub.6 H.sub.5       reddish violet                 1633                                                                              C.sub.3 H.sub.7 (n)                                                                 CH.sub.2CH.sub.2OH                                                                            ##STR768##           reddish violet                 1634                                                                              C.sub.3 H.sub.7 (n)                                                                 (CH.sub.2).sub.2O(CH.sub.2).sub.2OH                                                           ##STR769##           reddish violet                 __________________________________________________________________________

                                      TABLE 16                                    __________________________________________________________________________     ##STR770##                                                                   No.                                                                              A          R     X           Y          Shade                              __________________________________________________________________________    1635                                                                              ##STR771##                                                                              C.sub.2 H.sub.5                                                                     CH.sub.2CH.sub.2OH                                                                        C.sub.6 H.sub.5                                                                          orange                                CH.sub.2CH.sub.2                                                           1636                                                                              ##STR772##                                                                              C.sub.3 H.sub.7 (n)                                                                 CH.sub.2CH.sub.2OH                                                                        C.sub.6 H.sub.5                                                                          orange                                CH.sub.2CH.sub.2                                                           1637                                                                              ##STR773##                                                                              C.sub.3 H.sub.7 (n)                                                                 CH.sub.2CH.sub.2CH.sub.2 OH                                                               C.sub.6 H.sub.5                                                                          orange                             1638                                                                             CH.sub.3 OCOCH.sub.2 CH.sub.2                                                            C.sub.3 H.sub.7 (n)                                                                 CH.sub.2CH.sub.2OH                                                                         ##STR774##                                                                              orange                             __________________________________________________________________________

                                      TABLE 17                                    __________________________________________________________________________     ##STR775##                                                                   No.                                                                              A     X                  Y            Shade                                __________________________________________________________________________    1639                                                                             C.sub.3 H.sub.7 (n)                                                                 CH.sub.2CH.sub.2OH                                                                                ##STR776##  reddish orange                       1640                                                                             C.sub.3 H.sub.7 (n)                                                                 CH.sub.2CH.sub.2OH C.sub.6 H.sub.5                                                                            yellowish red                        1641                                                                             C.sub.2 H.sub.5                                                                     CH.sub.2CH.sub.2 OH                                                                              C.sub.6 H.sub.5                                                                            yellowish red                        1642                                                                             C.sub.2 H.sub.5                                                                     CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              C.sub.6 H.sub.5                                                                            yellowish red                        __________________________________________________________________________

                                      TABLE 18                                    __________________________________________________________________________     ##STR777##                                                                   No.                                                                              R     X                  Y            Shade                                __________________________________________________________________________    1643                                                                             C.sub.3 H.sub.7 (n)                                                                 CH.sub.2CH.sub.2OH                                                                                ##STR778##  orange                               1644                                                                             C.sub.3 H.sub.7 (n)                                                                 CH.sub.2CH.sub.2OH C.sub.6 H.sub.5                                                                            yellowish red                        1645                                                                             C.sub.2 H.sub.5                                                                     CH.sub.2CH.sub.2OH C.sub.6 H.sub.5                                                                            yellowish red                        1646                                                                             C.sub.2 H.sub.5                                                                     CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              C.sub.6 H.sub.5                                                                            yellowish red                        __________________________________________________________________________

                                      TABLE 19                                    __________________________________________________________________________     ##STR779##                                                                   No.                                                                              R     X                  Y            Shade                                __________________________________________________________________________    1647                                                                             C.sub.3 H.sub.7 (n)                                                                 CH.sub.2CH.sub.2OH                                                                                ##STR780##  orange                               1648                                                                             C.sub.3 H.sub.7 (n)                                                                 CH.sub.2CH.sub.2OH C.sub.6 H.sub.5                                                                            yellowish red                        1649                                                                             C.sub.2 H.sub.5                                                                     CH.sub.2CH.sub.2OH C.sub.6 H.sub.5                                                                            yellowish red                        1650                                                                             C.sub.2 H.sub.5                                                                     CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              C.sub.6 H.sub.5                                                                            yellowish red                        __________________________________________________________________________

                                      TABLE 20                                    __________________________________________________________________________     ##STR781##                                                                   No.                                                                              R     X                  Y            Shade                                __________________________________________________________________________    1651                                                                             C.sub.3 H.sub.6 (n)                                                                 CH.sub.2CH.sub.2OH                                                                                ##STR782##  yellow                               1652                                                                             C.sub.3 H.sub.7 (n)                                                                 CH.sub.2CH.sub.2OH C.sub.6 H.sub.5                                                                            orange                               1653                                                                             C.sub.2 H.sub.5                                                                     CH.sub.2CH.sub.2OH C.sub.6 H.sub.5                                                                            orange                               1654                                                                             C.sub.2 H.sub.5                                                                     CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                              C.sub.6 H.sub.5                                                                            orange                               __________________________________________________________________________

                                      TABLE 21                                    __________________________________________________________________________     ##STR783##                                                                   No.                                                                              R     X             Y          Shade                                       __________________________________________________________________________    1655                                                                             C.sub.2 H.sub.5                                                                     CH.sub.2CH.sub.2CH.sub.2OH                                                                  C.sub.6 H.sub.5                                                                          yellow to                                                                     orange                                      1656                                                                             C.sub.2 H.sub.5                                                                     CH.sub.2CH.sub.2OH                                                                          C.sub.6 H.sub.5                                                                          yellow to                                                                     orange                                      1657                                                                             C.sub.3 H.sub.7 (n)                                                                 H                                                                                            ##STR784##                                                                              yellow                                      1658                                                                             C.sub.3 H.sub.7 (n)                                                                  ##STR785##   H          yellow                                      1659                                                                             C.sub.3 H.sub.7 (n)                                                                  ##STR786##   CH.sub.2CH.sub.2OH                                                                       yellow                                      __________________________________________________________________________

                                      TABLE 22                                    __________________________________________________________________________     ##STR787##                                                                   No.                                                                              R     X             Y          Shade                                       __________________________________________________________________________    1660                                                                             C.sub.2 H.sub.5                                                                     CH.sub.2CH.sub.2CH.sub.2OH                                                                  C.sub.6 H.sub.5                                                                          yellow to                                                                     orange                                      1661                                                                             C.sub.2 H.sub.5                                                                     CH.sub.2CH.sub.2OH                                                                          C.sub.6 H.sub.5                                                                          yellow to                                                                     orange                                      1662                                                                             C.sub.3 H.sub.7 (n)                                                                 H                                                                                            ##STR788##                                                                              yellow                                      1663                                                                             C.sub.3 H.sub.7 (n)                                                                  ##STR789##   H          yellow                                      1664                                                                             C.sub.3 H.sub.7 (n)                                                                  ##STR790##   CH.sub.2CH.sub.2OH                                                                       yellow                                      __________________________________________________________________________

                                      TABLE 23                                    __________________________________________________________________________     ##STR791##                                                                   No.                                                                              R     X         Y             Shade                                        __________________________________________________________________________    1665                                                                             C.sub.3 H.sub.7                                                                     CH.sub.2CH.sub.2OH                                                                      (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5                                                    bluish red                                   1666                                                                             C.sub.3 H.sub.7 (n)                                                                 H         C.sub.6 H.sub.5                                                                             bluish red                                   __________________________________________________________________________

                                      TABLE 24                                    __________________________________________________________________________     ##STR792##                                                                   No.                                                                              R     X         Y             Shade                                        __________________________________________________________________________    1667                                                                             C.sub.3 H.sub.7 (n)                                                                 CH.sub.2CH.sub.2OH                                                                      (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5                                                    bluish red                                   1668                                                                             C.sub.3 H.sub.7                                                                     H         C.sub.6 H.sub.5                                                                             bluish red                                   __________________________________________________________________________

                                      TABLE 25                                    __________________________________________________________________________     ##STR793##                                                                   No.                                                                              R     X         Y             Shade                                        __________________________________________________________________________    1669                                                                             C.sub.3 H.sub.7 (n)                                                                 CH.sub.2CH.sub.2OH                                                                      (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5                                                    bluish red                                   1670                                                                             C.sub.3 H.sub.7 (n)                                                                 H         C.sub.6 H.sub.5                                                                             bluish red                                   __________________________________________________________________________

                                      TABLE 26                                    __________________________________________________________________________     ##STR794##                                                                   No.                                                                              R.sup.1      R.sup.2      R.sup.3                                                                           R.sup.4                                                                           Shade                                    __________________________________________________________________________    1671            (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OH                                                      C.sub.2 H.sub.5                                                                   CH.sub.3                                                                          pink                                     1672                                                                             H            (CH.sub.2).sub.3 O(CH.sub.2).sub.6 OH                                                      C.sub.3 H.sub.7                                                                   CH.sub.3                                                                          pink                                     1673                                                                             H            (CH.sub.2).sub.3 O(CH.sub.2).sub.6 OH                                                      CH.sub.3                                                                          CH.sub.3                                                                          pink                                     1674                                                                             H                                                                                           ##STR795##  CH.sub.3                                                                          CH.sub.3                                                                          pink                                     1675                                                                             H            (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OH                                                      CH.sub.3                                                                          CH.sub.3                                                                          pink                                     1676                                                                             H            (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5                                                 CH.sub.3                                                                          CH.sub.3                                                                          pink                                     1677                                                                             H                                                                                           ##STR796##  CH.sub.3                                                                          CH.sub.3                                                                          pink                                     1678                                                                             (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5                                                 CH.sub.2 CH.sub.2 OH                                                                       C.sub.2 H.sub.5                                                                   CH.sub.3                                                                          bluish red                               1679                                                                             (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5                                                 (CH.sub.2).sub.3 OH                                                                        C.sub.2 H.sub.5                                                                   CH.sub.3                                                                          bluish red                               1680                                                                             (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5                                                 (CH.sub.2).sub.3 OH                                                                        CH.sub.3                                                                          CH.sub.3                                                                          bluish red                               1681                                                                             (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5                                                 CH.sub.2 CH.sub.2 OH                                                                       CH.sub.3                                                                          CH.sub.3                                                                          bluish red                               1682                                                                             (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5                                                 CH.sub.2 CH.sub.2 OH                                                                       CH.sub.3                                                                          C.sub.2 H.sub.5                                                                   bluish red                               1683                                                                             (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5                                                 (CH.sub.2).sub.3 OH                                                                        CH.sub.3                                                                          C.sub.2 H.sub.5                                                                   bluish red                               1684                                                                              ##STR797##  (CH.sub.2).sub.3 OH                                                                        CH.sub.3                                                                          C.sub.2 H.sub.5                                                                   bluish red                               1685                                                                              ##STR798##  CH.sub.2 CH.sub.2 OH                                                                       CH.sub.3                                                                          C.sub.2 H.sub.5                                                                   bluish red                               1686                                                                              ##STR799##  CH.sub.2 CH.sub.2 OH                                                                       CH.sub.3                                                                          CH.sub.3                                                                          bluish red                               1687                                                                              ##STR800##  (CH.sub.2).sub.3 OH                                                                        C.sub.2 H.sub.5                                                                   CH.sub.3                                                                          bluish red                               __________________________________________________________________________

We claim:
 1. A dye of the formula ##STR801## wherein: D is phenylsubstituted by chlorine, bromine, trifluoromethyl, methyl, methoxy,nitro, cyano, methylsulfonyl, phenylsulfonyl, carbalkoxy of a total of 2to 5 carbon atoms, carbo-β-alkoxy-ethoxy, said alkoxy having 1 to 4carbon atoms, or N,N-dialkyl- or N-monoalkyl-substituted sulfamoyl, eachalkyl having 1 to 4 carbon atoms; phenylazophenyl; phenylazophenylsubstituted by methyl, chlorine, bromine or nitro; benzthiazolyl;benzthiazolyl substituted by nitro, cyano, methylsulfonyl orethylsulfonyl; benzisothiazolyl substituted by chlorine, bromine, cyanoor nitro; thiazolyl substituted by cyano or nitro; thienyl substitutedby methyl, cyano, nitro or carbalkoxy of a total of 2 to 5 carbon atoms;or thiadiazolyl substituted by phenyl, methyl, chlorine, bromine,methylmercapto, ethylmercapto or alkoxycarbonylethylmercapto, saidalkoxy having 1 to 4 carbon atoms;R is alkyl of 1 to 3 carbon atoms; Xis carbamoyl or cyano; R¹ and R² may be the same or different with theproviso that one of R¹ and R² is C₆ H₅ ; ##STR802## (CH₂)₃ OCH₂ CH₂ OH;(CH₂)₃ O(CH₂)₆ OH; ##STR803## (CH₂)₃ OC₂ H₄ OR⁷, (CH₂)₃ (OC₂ H₄)_(q)OR⁸, (CH₂)₃ OR⁹ ; ##STR804## C₂ H₄ OC₆ H₅, C₂ H₄ OC₆ H₄ CH₃ ; ##STR805##and the other of R¹ and R² is hydrogen; alkyl of 1 to 8 carbon atoms;alkyl of 2 to 8 carbon atoms substituted by hydroxy, alkoxy of 1 to 8carbon atoms, formyloxy, acetoxy, propionyloxy, carboxy, cyclohexoxy,benzyloxy, phenylethoxy, phenoxy or pyrrolidonyl; cyclohexyl;methylcyclohexyl; benzyl; phenylethyl; β-phenyl-β-hydroxyethyl; phenyl;tolyl; CH₂ CH₂ OCH₂ CH₂ OH; (CH₂)₃ OC₆ H₅ --CH₃ ; (CH₂)₃ O(CH₂)₄ OH;##STR806## (CH₂)₃ OC₂ H₄ OCH₃ ; (CH₂)₃ OC₂ H₄ OC₆ H₅ ; ##STR807## (CH₂)₃OCH₂ CH₂ OH; (CH₂)₃ O(CH₂)₆ OH; ##STR808## (CH₂)₃ OC₂ H₄ OR⁷ ; (CH₂)₃(oc₂ H₄)_(q) OR⁸ ; ##STR809## C₂ H₄ OC₆ H₄ CH₃ ; ##STR810## R³ is alkylof one to three carbon atoms, hydroxymethyl or hydroxyethyl; R⁴ ishydrogen, alkyl of one to three carbon atoms, hydroxymethyl orhydroxyethyl; R⁵ is hydrogen or hydroxyl; R⁶ is hydrogen, alkyl of 1 to4 carbon atoms, methoxy, ethoxy or chloro; one of R³ to R⁵ providing ahydroxy group; R⁷ is ethyl, propyl, butyl, cyclohexyl, benzyl,phenylethyl or methylphenyl; R⁸ is hydrogen, alkyl of one to four carbonatoms, cyclohexyl, phenyl, methylphenyl, benzyl or phenylethyl; R⁹ iscyclohexyl, phenyl, methylphenyl, benzyl or phenylethyl; m is 1 or 2; nis zero, 1 or 2; q is 2, 3 or 4; and p is 1, 2, 3 or
 4. 2. A dye asclaimed in claim 1 of the formula ##STR811## wherein: Y is nitro, cyano,chloro, bromo, carbomethoxy, carboethoxy, β-methoxycarboethoxy,methylsulfonyl, ethylsulfonyl, methyl, methoxy or phenylazo;Y¹ ishydrogen, nitro, chloro, bromo, cyano, methyl, methoxy, carbomethoxy,carboethoxy, methylsulfonyl or ethylsulfonyl; and Y² is hydrogen,chloro, bromo, cyano, methyl, methoxy, carbomethoxy or carboethoxy; andR¹ and R² have the same meanings as given in claim
 1. 3. A dye asclaimed in claim 1 wherein X is cyano.
 4. A dye as claimed in claim 1wherein:X is cyano; said one of R¹ and R² is C₆ H₅ ; ##STR812## (CH₂)₃OC₂ H₄ OH, (CH₂)₃ O(CH₂)₆ OH, ##STR813## (CH₂)₃ OC₂ H₄ OCH₂ C₆ H₅ ;(CH₂)₃ (OC₂ H₄)₂ OR⁸ ; ##STR814## (CH₂)₃ OC₆ H₅ ; (CH₂)₃ OCH₂ C₆ H₅ or(CH₂)₃ OC₂ H₄ C₆ H₅ ; andsaid other of R¹ and R² is hydrogen; or alkylof 2 to 8 carbon atoms substituted by hydroxy, alkoxy of 1 to 4 carbonatoms, formyloxy, acetoxy or propionyloxy.
 5. The dye of the formula##STR815##
 6. The dye of the formula ##STR816##
 7. The dye of theformula ##STR817##
 8. The dye of the formula ##STR818##